Fused heterocyclic compound, pyrazole-ring-containing fused heterocyclic compound, agricultural composition containing thereof, and method of using the composition

ABSTRACT

A fused tricyclic compound, an optical isomer, cis and trans isomers or an agromedically acceptable salt thereof, and insecticidal use thereof in agroforestry. A pyrazole-ring-contained fused heterocyclic compound, an agricultural composition, and a method of using the agricultural composition are also provided.

TECHNICAL FIELD

The present invention belongs to the field of heterocyclic compounds,and more particularly, relates to a fused heterocyclic compound, and anoptical isomer, cis and trans isomers or an agromedically acceptablesalt thereof, as well as a preparation method and use thereof.

BACKGROUND

New heterocyclic pesticides represented by nitrogen-containingheterocycles have the advantages of high insecticidal activity, wideinsecticidal spectrum, low toxicity to mammals and appropriate fieldstability, so that heterocyclic compounds have become an importanthotspot field in the development of new pesticides. In recent years,newly developed pesticides such as Flupyrimin, flupyradifurone,cycloxaprid, sulfoxaflor, flonicamid, spirotetramat, cyflumetofen,cyenopyrafen, cyantraniliprole and the like, all belong to thenitrogen-containing heterocyclic compounds (with reference to patentsUS2013150414, CN103960242, CN103254125, CN102892290, DE102006015467,WO2010069266, WO2007095229, EP580374, WO9805638, WO2002014263,JP2003201280 and WO2004067528).

However, the problems of serious resistance and cross resistance arecaused due to excessive and frequent use of a single pesticide and ahigh toxicity of the existing insecticide to the environment whilekilling pests, which reduces an efficacy of the pesticide and greatlyrestricts use of the pesticide, thus restricting the development ofagriculture and forestry. Therefore, how to develop a new pesticide thatis more efficient and environmentally friendly and how to solve theproblem of resistance become technical problems to be urgently solved inthis field.

New structural molecules with big structural differences from previouspesticide molecules are believed to have no cross resistance with theexisting pesticides, and may be used to control the development of pestresistance (Pestide Biochemistry and Physiology, 2015, 121: 22). Inrecent years, multiple series of fused heterocyclic compounds have beensynthesized and reported to have an extensive bioactivity (such asComputational Biology and Chemistry, 2018, 74: 218; Bioorganic &Medicinal Chemistry Letters, 2017, 27: 3201; Journal of MedicinalChemistry, 2017, 60: 9691; Journal of Heterocyclic Chemistry, 2017, 54:2788; Organic & Biomolecular Chemistry, 2016, 14: 8721; Journal ofEnzyme Inhibition and Medicinal Chemistry, 2015, 31: 195; New Journal ofChemistry, 2015, 39: 1060; Chemistry-A European Journal, 2015, 21:16859; Bioorganic & Medicinal Chemistry Letters, 2014, 24: 2693; Journalof Medicinal Chemistry, 2013, 56: 7458; Bioorganic & Medicinal ChemistryLetters, 2009, 19: 4196; Chemistry & Biology, 2007, 14: 153; Journal ofBiological Chemistry, 2003, 278: 25990; and Journal of MedicinalChemistry, 2002, 45: 1035). Based on this, a large number of new fusedheterocyclic compounds have been designed, synthesized and screened inthis study. These compounds with novel structures have excellent controleffects on a variety of pests and even on pests with resistance.

SUMMARY

An object of the present invention is to provide a nitrogen-containingfused tricyclic compound, and an optical isomer, cis and trans isomersor an agromedically acceptable salt thereof. The fused heterocycliccompound and the optical isomer, the cis and trans isomers or theagromedically acceptable salt thereof have a high killing activity onagroforestry pests and sanitary insect pests and sanitary pests, andmore surprisingly, have a delayed working effect on pests such asSolenopsis invicta, thereby having a better killing effect.

Another object of the present invention is to provide a method forpreparing the fused tricyclic compound, and the optical isomer, the cisand trans isomers or the agromedically acceptable salt thereof.

Another object of the present invention is to provide use of the fusedheterocyclic compound and the optical isomer, the cis and trans isomersor the agromedically acceptable salt thereof in preparing aninsecticide.

In order to achieve the above objects, the technical solutions adoptedby the present invention are as follows.

A fused heterocyclic compound, and an optical isomer, cis and transisomers or an agromedically acceptable salt thereof, wherein the fusedheterocyclic compound has a structure shown in formula (I):

wherein R¹¹ and R¹² are each independently hydrogen, halogen, —NO₂, —CN,—COR¹⁷, —CO₂R¹⁷, —CONR¹⁷R¹⁸, —S(O) R¹⁷, —S(O)₂ R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷COR¹⁸, —N R¹⁷CON R¹⁸R¹⁹, —N R¹⁷CO₂ R¹⁸, —N R¹⁷S(O)₂ R¹⁸, alkyl,heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl orheteroaryl; wherein the alkyl, the alkenyl, the cycloalkyl, thecycloalkenyl, the aryl, the heterocyclyl or the heteroaryl isunsubstituted or substituted with one or more substituents R¹⁰; and

R¹³ is hydrogen, —COR¹⁷, —CO₂ R¹⁷, —S(O)₂ R¹⁷, —CONR¹⁷R¹⁸, alkyl,heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl and aryl; wherein thealkyl, the alkenyl, the cycloalkyl, the cycloalkenyl and the aryl areunsubstituted or substituted with one or more substituents R¹⁰;

R¹⁴ and R¹⁵ are each independently hydrogen, halogen, —CN, —OH, —N R¹⁷R¹⁸, —O R¹⁷, —CO R¹⁷, —CO₂ R¹⁷, —CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CONR¹⁸R¹⁹, —NR¹⁷CO₂R¹⁸, —NR¹⁷S(O)₂R¹⁸, —S(O)R¹⁷, —S(O)₂R¹⁷, alkyl,heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl orheteroaryl; wherein the alkyl, the alkenyl, the cycloalkyl, thecycloalkenyl, the aryl, the heterocyclyl or the heteroaryl isunsubstituted or substituted with one or more substituents R¹⁰, and R¹⁴and R¹⁵ are not hydrogen at the same time;

Y is N or CH;

Z¹, Z², Z³ and Z⁴ are each independently C or N, under conditions thatat most two of Z¹ to Z⁴ are N, and a ring containing Z¹ to Z⁴ isaromatic;

R¹⁶ represents a substituent on the ring containing Z¹ to Z⁴, one ormore R¹⁶ are provided, and each R¹⁶ is independently hydrogen, halogen,—CN, alkyl, heteroalkyl, —CO R¹⁷, —CO₂ R¹⁷, —N R¹⁷ R¹⁸, —CONR¹⁷R¹⁸, —NR¹⁷CO R¹⁸, —NR¹⁷CON R¹⁸R¹⁹, —NR¹⁷CO₂R¹⁸ or —NR¹⁷S(O)₂R¹⁸;

R¹⁷, R¹⁸ and R¹⁹ are each independently hydrogen, alkyl, heteroalkyl,alkenyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl;wherein the alkyl, the alkenyl, the cycloalkyl, the cycloalkenyl, thearyl, the heterocyclyl or the heteroaryl is unsubstituted or substitutedwith one or more substituents R¹⁰; and

R¹⁰ is halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, substituted or unsubstitutedcycloalkyl, cycloalkenyl, substituted or unsubstituted aryl, substitutedor unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl,—CN, —NH₂, —OR′″, —NR′″R″″, —COR′″, —CO₂R′″, —CONR′″R″″, —NR′″COR″″,—NR′″CONR′″R″″, —NR′″CO₂R″″, —S(O)₂R′″ or —NR′″S(O)₂R″″, wherein R′″ andR″″ are each independently hydrogen, C₁-C₆ alkyl, C₂-C₆ alkenyl,cycloalkyl, cycloalkenyl, aryl, heteroaryl or heterocyclyl.

Preferably, when Y is N or CH;

R¹¹ is halogen, —CN, —COR¹⁷, —CONR¹⁷R¹⁸, —S(O) R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷COR¹⁸, aryl, heterocyclyl or heteroaryl; wherein the alkyl, theheterocyclyl or the heteroaryl is unsubstituted or substituted with oneor more substituents R¹⁰;

R¹² is hydrogen, —COR¹⁷, —CONR¹⁷R¹⁸, —S(O)R¹⁷, —S(O)₂R¹⁷, —N R¹⁷ R¹⁸, —NR¹⁷CO R¹⁸, —NR¹⁷CONR¹⁸R¹⁹, —NR¹⁷CO₂R¹⁸, aryl, heterocyclyl orheteroaryl; wherein the alkyl, the heterocyclyl or the heteroaryl isunsubstituted or substituted with one or more substituents R¹⁰;

R¹³ is hydrogen, —COR¹⁷, alkyl, heteroalkyl or alkenyl;

R¹⁴ is halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷, —CO R¹⁷, —CO₂ R¹⁷, —CONR¹⁷R¹⁸,—N R¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl or alkenyl; wherein thealkyl, the heteroalkyl or the alkenyl is unsubstituted or substitutedwith one or more substituents R¹⁰; and

R¹⁵ is hydrogen, halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷, —CO R¹⁷, —CO₂ R¹⁷,—CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl or alkenyl;wherein the alkyl, the heteroalkyl or the alkenyl is unsubstituted orsubstituted with one or more substituents R¹⁰.

Preferably, when Z¹, Z², Z³ and Z⁴ are all C, one or more R¹⁶ areprovided, and each R¹⁶ is independently hydrogen, halogen, alkyl,heteroalkyl, alkenyl, —S(O) R¹⁷, —S(O)₂ R¹⁷, —COR¹⁷, —N R¹⁷ R¹⁸,—CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸ or —NR¹⁷S(O)₂R¹⁸;

R¹¹ is halogen, —CN, —COR¹⁷, —CONR¹⁷R¹⁸, —S(O) R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷COR¹⁸, aryl, heterocyclyl or heteroaryl; wherein the alkyl, theheterocyclyl or the heteroaryl is unsubstituted or substituted with oneor more substituents R¹⁰;

R¹² is —CONR¹⁷R¹⁸, —S(O) R¹⁷, —S(O)₂ R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CON R¹⁸R¹⁹, aryl, heterocyclyl or heteroaryl; wherein the alkyl, theheterocyclyl or the heteroaryl is unsubstituted or substituted with oneor more substituents R¹⁰;

R¹³ is hydrogen, —COR¹⁷, alkyl or alkenyl; and

R¹⁴ and R¹⁵ are each independently halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷, —COR¹⁷, —CO₂ R¹⁷, —CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyland alkenyl; wherein the alkyl, the heteroalkyl and the alkenyl areunsubstituted or substituted with one or more substituents R¹⁰.

More preferably,

when Y is N or CH;

R¹¹ is halogen, —CN, —COR¹⁷, —CONR¹⁷R¹⁸, —S(O) R¹⁷, —N R¹⁷ R¹⁸ or —NR¹⁷CO R¹⁸;

R¹² is —S(O) R¹⁷, —S(O)₂ R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸, aryl orheteroaryl; wherein the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R¹⁰;

R¹³ is hydrogen, —COR¹⁷, alkyl or alkenyl;

R¹⁴ and R¹⁵ are each independently halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷, —COR¹⁷, —CO₂ R¹⁷, —CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkylor alkenyl; wherein the alkyl or the alkenyl is unsubstituted orsubstituted with one or more substituents R¹⁰; and

Z¹, Z², Z³ and Z⁴ are all C, one or more R¹⁶ are provided, and each R¹⁶is independently halogen, alkyl, heteroalkyl, —S(O) R¹⁷, —S(O)₂ R¹⁷,—COR¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸ or —NR¹⁷S(O)₂R¹⁸.

More preferably,

R¹¹ is halogen, —CN, —COR¹⁷ or —CONR¹⁷R¹⁸;

R¹² is —S(O)R¹⁷, —S(O)₂R¹⁷, —NR¹⁷COR¹⁸, aryl or heteroaryl; wherein thearyl or the heteroaryl is unsubstituted or substituted with one or moresubstituents R¹⁰;

R¹³ is hydrogen, —COR¹⁷ or alkyl; and

Z¹, Z², Z³ and Z⁴ are all C, one or more R¹⁶ are provided, and each R¹⁶is independently halogen, heteroalkyl, —S(O)R¹⁷, —NR¹⁷R¹⁸ or —NR¹⁷COR¹⁸.

More preferably,

R¹¹ is —CN or —COR¹⁷;

R¹² is —S(O)R¹⁷ or aryl; wherein the aryl is substituted with one ormore substituents R¹⁰;

R¹³ is hydrogen, —COR¹⁷, methyl or ethyl;

R¹⁴ and R¹⁵ are each independently halogen, —OR¹⁷, —COR¹⁷, —CO₂R¹⁷,—CONR¹⁷R¹⁸, —NR¹⁷COR¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl or alkenyl;wherein the alkyl or the alkenyl is unsubstituted or substituted withone or more substituents R¹⁰; and

Z¹, Z², Z³ and Z⁴ are all C, one or more R¹⁶ are provided, and each R¹⁶is independently halogen or heteroalkyl.

More preferably,

R¹¹ is —CN or —COR¹⁷, and R¹⁷ is alkyl or heteroalkyl;

R¹² is —S(O)R¹⁷, and R¹⁷ is alkyl or heteroalkyl;

R¹³ is hydrogen, —COR¹⁷, methyl or ethyl, and R¹⁷ is alkyl;

R¹⁴ and R¹⁵ are each independently halogen, —OR¹⁷, —COR¹⁷, —CO₂R¹⁷,—CONR¹⁷R¹⁸, —NR¹⁷COR¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl or alkenyl;wherein the alkyl or the alkenyl is unsubstituted or substituted withone or more substituents R¹⁰; and

Z¹, Z², Z³ and Z⁴ are all C, one or more R¹⁶ are provided, and each R¹⁶is independently halogen or heteroalkyl.

The present invention further discloses a pyrazole-ring-containing fusedheterocyclic compound, and an optical isomer, cis and trans isomers oran agromedically acceptable salt thereof, wherein thepyrazole-ring-containing fused heterocyclic compound has a structureshown in formula (II):

wherein R¹ is hydrogen, halogen, —CN, alkyl, heteroalkyl, aryl orheteroaryl; wherein the alkyl, the aryl or the heteroaryl isunsubstituted or substituted with one or more substituents R⁹; and

R² is hydrogen, halogen, —CN, —S(O)R⁷, —S(O)₂R⁷, alkyl, heteroalkyl,aryl or heteroaryl; wherein the alkyl, the aryl or the heteroaryl isunsubstituted or substituted with one or more substituents R⁹; and

R³ is hydrogen, —COR⁷, alkyl or heteroalkyl;

R⁴ and R⁵ are each independently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷,—CH₂COR⁷, —CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl;wherein the amino, the alkyl, the aryl or the heteroaryl isunsubstituted or substituted by one or more substituents R⁹, and R⁴ andR⁵ are not hydrogen at the same time;

Z¹ and Z² are independently C or N, and are not N at the same time, anda ring containing Z¹ and Z² is an aromatic ring;

R⁶ represents a substituent on the ring containing Z¹ and Z², one ormore R⁶ are provided, and each R⁶ is independently hydrogen, halogen,—NO₂, —CN, alkyl, heteroalkyl, —OR⁷, —COR⁷, —CO₂R⁷ or —NR⁷R⁸;

R⁷ and R⁸ are each independently hydrogen, hydroxyl, amino, C₁-C₆ alkyl,heteroalkyl, aryl or heteroaryl; wherein the alkyl, the aryl or theheteroaryl is unsubstituted or substituted with one or more substituentsR⁹; and

R⁹ is halogen, C₁-C₆ alkyl, heteroalkyl, —CN, —NH₂, —OH, —COR′, —CO₂R′or —CONR′R″, wherein R′ and R″ are each independently hydrogen, C₁-C₆alkyl or heteroalkyl.

Preferably, when Z¹ is N and Z² is C, R⁶ is a monosubstituent —CF₃ at a5-position of a pyridine ring, and a general formula of the compound isshown in formula (a):

wherein R³ is hydrogen, methyl or chloromethyl; R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹;

or,

when Z² is N and Z¹ is C, R⁶ is a monosubstituent chlorine at a5-position of the pyridine ring, and a general formula of the compoundis shown in formula (b):

wherein R³ is hydrogen, methyl or chloromethyl; R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹;

or,

when Z¹ and Z² are both C, and R⁶ is disubstituents at a 3-position anda 5-position of a benzene ring, a general formula of the compound isshown in formula (c):

wherein R¹ is —CN or —CF₃, and R² is —CN, —CF₃, —OCF₃, —SOCF₃ or—SOCH₂CH₃; R³ is hydrogen, —CH₃, —Ac or —CH₂CH₂Cl; a substituent of R⁶at the 3-position of the benzene ring is —Cl, —Br, —CF₃, —CH₃, —CN,—CO₂CH₃ or —NO₂, and a substituent of R⁶ at the 5-position of thebenzene ring is —Cl, —CF₃, —OCF₃ or —NO₂; R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹;

or,

when Z¹ and Z² are both C, R⁶ is disubstituents at a 4-position and a6-position of the benzene ring, and R³ is hydrogen, the general formulaof the compound is shown in formula (d):

wherein R¹ is —CN, —CF₃, —CHO or —CH₂NH₂, and R² is —OCF₃, —CF₃, —CN,—SOCF₃, —SOCH₃, —SOCH₂CH₃, —SOPh, —SOCH₂Ph, —SOC₆H₁₃,

R⁶ is —Cl or —CF₃; R⁴ and R are each independently hydrogen, halogen,—CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷, —CH₂COOR⁷, amino, alkyl, heteroalkyl, arylor heteroaryl; wherein the amino, the alkyl, the aryl or the heteroarylis unsubstituted or substituted with one or more substituents R⁹;

or,

when Z¹ and Z² are both C, R⁶ is disubstituents at the 3-position andthe 6-position, or at the 3-position and the 4-position, or at the4-position and the 5-position, or at the 5-position and the 6-positionof the benzene ring, the general formula of the compound is shown informula (e):

wherein R¹ is —CN, and R² is —SOCF₃; R⁶ is —Cl or —CF₃; R⁴ and R⁵ areeach independently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹; and R⁴ and R⁵ are nothydrogen at the same time.

Preferably, R⁴ and R⁵ are each independently hydrogen, halogen, —CN,—COR⁷, —CO₂R⁷, —CH₂COR⁷, —CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl orheteroaryl; wherein R⁷ is hydrogen, halogen, hydroxyl, C₁₋₄ alkyl, C₁₋₄haloalkyl, C₁₋₄ alkenyl, C₁₋₄ haloalkenyl, amino or substituted amino.

Preferably, when the compound is shown in the formula (a) or the formula(b), and any one of R⁴ and R⁵ is hydrogen, R¹ is —CN, and R² is —SOCF₃or —OCF₃; or R¹ is —CF₃, and R² is —SOCF₃;

or, when neither R⁴ nor R⁵ is hydrogen, R¹ is —CN or —CF₃; and R² is—SOCF₃, —SOCH₂CH₃, —OCF₃, —CF₃, —CN or halogen.

Preferably, when the compound is shown in the formula (c), R³ is —CH₃,—Ac or —CH₂CH₂Cl, R² is —SOCF₃, R¹ is —CN, and both R⁴ and R⁵ are—CO₂Me;

or, when R³ is hydrogen, and R² is —CN, —CF₃ or —SOCH₂CH₃, R¹ is —CN or—CF₃, and R⁴ and R⁵ are independently —CO₂Me or —CH₂CO₂Me;

or, when R³ is hydrogen, and R² is —OCF₃ or —SOCF₃, R¹ is —CN or —CF₃,R⁴ and R⁵ are each independently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷,—CH₂COR⁷, —CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl;wherein the amino, the alkyl, the aryl or the heteroaryl isunsubstituted or substituted with one or more substituents R⁹.

Preferably, when the compound is shown in the formula (d), R³ ishydrogen, and R² is —CN, —CF₃, —SOPh, —SOCH₂Ph, —SOC₆H₁₃,

R¹ is —CN, and R⁴ and R⁵ are independently —CO₂Me or —CO₂CH₂Me;

or, when R³ is hydrogen, R² is —SOCF₃, and R¹ is —CHO or —CH₂NH₂, R⁴ andR⁵ are independently —CO₂Me or —CO₂CH₂Me;

or, when R³ is hydrogen, and R² is —OCF₃ or —SOCF₃, R¹ is —CN or —CF₃,R⁴ and R⁵ are independently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷,—CH₂COR⁷, —CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl;wherein the amino, the alkyl, the aryl or the heteroaryl isunsubstituted or substituted with one or more substituents R⁹.

Preferably, when the compound is shown in the formula (e), R⁶ is 3-Cland 6-CF₃, 3-Cl and 4-CF₃, 4-Cl and 5-CF₃, or 5-Cl and 6-CF₃ on thebenzene ring; and R⁴ and R⁵ are each independently —CO₂Me, —CH₂CO₂Me,—CO₂Et, —CH₂CO₂Et, —CH₂CO₂CH₂CF₃ or —CH₂CO₂CH₂CHF₂.

An agricultural composition includes:

(a) 0.001 to 99.99% by weight of the compound above, the optical isomer,the cis and trans isomers or the agromedically acceptable salt thereof,or a combination thereof; and

(b) an agromedically acceptable carrier and/or excipient.

Use of the agricultural composition according to the present inventionin preparing an insecticide for killing or preventing agroforestrypests, sanitary insect pests and pests harmful to animal health.

A specific use method is that the insecticide is directly applied to thepests or places contacted by the pests (for example, plants sufferingfrom or probably suffering from pest damages, soil or environmenttherearound).

Compared with the prior art, the present invention has the followingbeneficial effects.

The present invention discloses the fused heterocyclic compounds with anew structure and the pyrazole-ring-containing fused heterocycliccompound. The fused heterocyclic compound and thepyrazole-ring-containing fused heterocyclic compound, and the opticalisomer, cis and trans isomers or the agromedically acceptable saltthereof have high killing activity on agroforestry pests and sanitaryinsect pests and the like, and the compound according to the presentinvention has a delayed effect on pests such as Solenopsis invicta andthe like, which enables the pests to carry the compound to a nest,thereby having a better killing effect on the whole Solenopsis invictanest and a queen Solenopsis invicta. The compound according to thepresent invention has a good application prospect in pest control. Thecompound according to the present invention has lower toxicity toenvironmental organisms such as bees, Bombyx mori L. and the like, thushaving a good application prospect.

DETAILED DESCRIPTION

The inventor of the present invention designs, synthesizes and screens anew fused heterocyclic compound and a pyrazole-ring-containing fusedheterocyclic compound based on the problems of increasingly seriousresistance and harmness to the environment and the like of the existingheterocyclic pesticides upon long-term and in-depth research. Aninsecticidal activity of the compound is obviously improved, and thecompound has an expanded insecticidal spectrum. The present invention isfurther illustrated hereinafter with reference to the specificembodiments, but the embodiments are not intended to limit the presentinvention in any form. Unless otherwise specified, all the reagents andmethods involved in the embodiments are frequently-used reagents andmethods in the field.

In the present invention, unless otherwise specified in the context,meanings expressed by words, phrases and symbols to be used below areregulated as follows. The meanings of the following abbreviations andterms are used throughout the text.

The term “halogen” refers to fluorine, chlorine, bromine and iodine, andthe term “halogen” in front of a group name refers to that the group ispartially or completely halogenated, i.e., the group is substituted byF, Cl, Br or I in any combination, for example,monofluorodichloromethyl, difluoromethyl, trichloromethyl,pentafluoroethyl, or similar groups.

The term “alkyl” refers to hydrocarbyl, and the hydrocarbyl is selectedfrom a saturated linear-chain or branched-chain hydrocarbyl. The alkylpreferably includes 1 to 12 carbon atoms, and more preferably includes 1to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl,isobutyl, sec-butyl, tert-butyl, or similar groups.

The term “alkenyl” refers to a hydrocarbyl selected from a linear-chainor a branched-chain, and includes at least one C═C double bond. Thealkenyl preferably includes 2 to 12 carbon atoms, and more preferablyincludes 2 to 6 carbon atoms, such as vinyl, prop-1-alkenyl,prop-2-alkenyl, 2-methylprop-1-alkenyl, buta-1,3-dialkylene,2-methyl-1,3-butadiene, hex-1,3-dialkylene, or similar groups.

The term “cycloalkyl” refers to be selected from to a saturatedcyclohydrocarbyl, and includes a monocyclic or polycyclic group. Thecycloalkyl preferably has 3 to 12 carbon atoms. For example, thecycloalkyl may be a monocyclic group having 3 to 12 carbon atoms, suchas cyclopropyl, cyclobutyl, cyclopentyl, cyclononyl, cyclodecyl,cycloundecyl and cyclododecyl, or similar groups. The cycloalkyl mayalso be a bicyclic group having 4 to 12 carbon atoms, such as a bicyclicgroup in [4,5], [5,5], [5,6] and [6,6] ring systems, a bridged bicyclicgroup selected from bicyclic[2.2.1]heptane, bicyclic[2.2.2]octane andbicyclic[3.2.2]nonane, or similar groups.

The term “cycloalkenyl” refers to be selected from an unsaturatedcyclohydrocarbyl, and contains at least one C═C double bond, but is notcompletely conjugated, and the cycloalkenyl does not belong to anaromatic series (the aromatic series as defined herein), and includes amonocyclic or polycyclic group. The cycloalkenyl preferably has 3 to 12carbon atoms, such as cyclopentene, cyclopentadiene, cyclohexene,cyclohexadiene, cycloheptene, cyclooctene, and cyclopentadiene, orsimilar groups.

The term “aryl” refers to be selected from the groups as follows: (a) 5membered and 6 membered carbocyclic aromatic rings, such as phenyl,furan ring or thiophene ring; (b) bicyclic systems such as 7 to 12membered bicyclic systems, wherein at least one ring is a carboatomicring and an aromatic ring, such as naphthalene or1,2,3,4-tetrahydroquinoline; (c) tricyclic systems, such as a 10 to 15membered tricyclic systems, wherein at least one ring is a carboatomicring and an aromatic ring, such as fluorene.

For example, the aryl is selected from 5-membered and 6-memberedcarbocyclic aromatic rings, wherein the carbocyclic aromatic ring isfused to 5 to 7 membered cycloalkyl or a heterocycle optionallycontaining at least one heteroatom selected from N, O and S, under theconditions that a connection point is on the carbocyclic aromatic ringwhen the carbocyclic aromatic ring is fused to the heterocycle, and theconnection point may be on the carbocyclic aromatic ring or on thecycloalkyl when the carbocyclic aromatic ring is fused to thecycloalkyl. A divalent group formed from a substituted benzenederivative and having a free valence on a ring atom is called asubstituted phenylene group. A divalent group derived from a monovalentpolycyclic hydrocarbon with a name ended with “yl” by removing ahydrogen atom from a carbon atom having a free valence is named byadding “subunit” to the name of the corresponding monovalent group, forexample, a naphthyl having two connection points is called anaphthylene. However, the aryl does not include heterocyclyl or overlapswith heteroaryl, which are defined separately below. Therefore, if oneor more carbocyclic aromatic rings are fused with a heterocyclicaromatic ring, a resulting ring system is the heteroaryl as definedherein, rather than the aryl.

The term “heteroalkyl” refers to an alkyl including at least oneheteroatom, and the heteroatom refers to a non-C atom. The heteroatom ispreferably N, O, S, P or Se, etc.

The term “heteroaryl” refers to be selected from the groups as follows:

5 to 7 membered aromatic monocyclic ring containing 1, 2, 3 or 4heteroatoms selected from N, O and S, and the rest ring atoms beingcarbon;

8 to 12 membered bicyclic ring containing 1, 2, 3 or 4 heteroatomsselected from N, O and S, the remaining ring atoms being carbon, andwherein at least one ring is aromatic and at least one heteroatom ispresent in the aromatic ring;

11 to 14 membered bicyclic ring containing 1, 2, 3 or 4 heteroatomsselected from N, O and S, the remaining ring atoms being carbon, andwherein at least one ring is aromatic and at least one heteroatom ispresent in the aromatic ring;

For example, the heteroaryl includes a 5 to 7 membered heterocyclicaromatic ring fused to a 5 to 7 membered cycloalkyl ring. For the fusedbicyclic heteroaryl ring system, only one ring therein contains at leastone heteroatom, and a connection point may be located on theheterocyclic aromatic ring or the cycloalkyl ring.

When a total number of Sand O atoms in the heteroaryl exceeds 1, theseheteroatoms are not adjacent to each other.

The term “heterocyclyl” refers to be selected from the rings as follows:saturated and partially unsaturated rings of 4 to 12 memberedmonocyclic, bicyclic and tricyclic rings, which contain at least onecarbon atom in addition to 1, 2, 3 or 4 heteroatoms selected fromoxygen, sulfur and nitrogen. The term “heterocyclyl” also refers to analiphatic spiro ring containing at least one heteroatom selected from N,O and S under the condition that a connection point is located on aheterocycle. The ring may be saturated or contain at least one doublebond. The heterocycle may be oxidatively substituted. A connection pointmay be a carbon atom or a heteroatom in the heterocycle.

The term “alkoxy” refers to a hydrocarbonoxy selected from saturatedlinear or branched hydrocarbonoxy. The alkoxy includes 1 to 12 carbonatoms, and preferably includes 1 to 6 carbon atoms, such as methoxyl,ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy,tert-butoxy, or similar groups.

The substituents are selected from halogen, —R″″, —OR″″, ═O, ═NR′″″,═N—OR′″″, —NR′″″R″″″, —SR′″″, —OC(O)R′″″, —C(O)R′″″, —CO₂R″″,—CONR′″″R″″″, —OC(O)NR′″″R″″″, —NR′″″C(O)R″″″, —NR′″″—SO₂NR″″″,—NR″″″CO₂R′″″, —NH—C(NH₂)═NH, —NR′″″C(NH₂)═NH, —NH—C(NH₂)═NR′″″,—S(O)R′″″, —SO₂R′″″, —SO₂NR″″R″″″, —NR″″″SO₂R′″″, —CN and —NO₂,—CH(Ph)₂, halogenated (C₁-C₄) alkoxy and halogenated (C₁-C₄)alkyl. Anumber of the substituents ranges from 0 to 3, and preferably, 0, 1 or 2substituents are provided. R′″″ and R′″″ are independently selected fromhydrogen, unsubstituted (C₁-C₆) alkyl and heteroalkyl, unsubstitutedaryl, aryl substituted with 1 to 3 halogens, unsubstituted alkyl, alkoxyor thioalkoxy, or aryl-(C₁-C₄) alkyl. When being connected to the samenitrogen atom, R′″″ and R″″″ can combine with the nitrogen atom to forma 5, 6 or 7 membered ring. Therefore, —NR′″″R′″″ includes 1-pyrrolidinyland 4-morpholinyl. The “alkyl” includes, for example, trihaloalkyl(e.g., —CF₃ and —CH₂CF₃).

Preferably, the substituents are selected from halogen, —R′″″, —OR′″″,═O, —NR′″″R″″″, —SR′″″, —OC(O)R′″″, —C(O)R′″″, —CO₂R′″″, —CONR′″″R″″″,—OC(O)NR′″″R″″″, —NR″″″C(O)R′″″, —NR″″″CO₂R′″″, —S(O)R′″″, —SO₂R′″″,—SO₂NR′″″R″″″, —NR″″″SO₂R′″″ —CN and —NO₂, halogenated (C₁-C₄) alkoxyand halogenated (C₁-C₄) alkyl, wherein R′″″ and R″″″ are defined asabove.

The term“fused heterocycle” herein refers to a following cyclic system,such as a bicyclic or tricyclic system, in which two rings share onlytwo ring atoms and one bond, and the ring atoms thereof contain at leastone non-C atom. Examples of the fused heterocycle may include fusedbi-heterocycloalkyl, such as bi-heterocycles selected from the above[4,4], [4,5], [5,5], [5,6] and [6,6] ring systems composed byarrangement of 7 to 12 ring atoms; fused bicyclic heteroaryl rings, suchas the 8 to 12 membered bicyclic heteroaryl rings described above; fusedtricyclic heteroaryl rings, such as the 11 to 14 membered tricyclicheteroaryl rings described above, for example,pyrazolo[1,5-a]quinazoline, pyrazolo[1,5-c]quinazoline,pyrrolo[1,2-a]quinazoline, pyrazolo[1,5-a]pyrido[3,2-e]pyrimidine,pyrazolo[1,5-a]pyrido[3,4-e]pyrimidine,pyrazolo[1,5-a]pyrido[2,3-e]pyrimidine, andpyrazolo[1,5-a]pyrido[4,3-e]pyrimidine, etc.; and the fused bicyclic ortricyclic heterocyclic rings.

The compound may contain an asymmetric center, and thus may exist as anenantiomer. When the compound has two or more asymmetric centers, theymay additionally exist as diastereomers. The enantiomers and thediastereomers belong to a broader category of stereomers. All thesepossible stereomers include substantially pure resolved enantiomers(meaning that a target stereomer contains no more than 10% by weight ofany other stereomer), racemic mixtures thereof, and diastereomericmixtures thereof. Unless otherwise stated, one of the mentioned isomersapplies to any possible isomer. When isomer components are notspecified, all possible isomers are included.

When the compound contains olefinic double bonds, these double bondsrefer to geometric isomers containing E and Z, unless otherwise stated.

Some compounds may have different hydrogen connection points, which arecalled tautomers. For example, a compound containing acarbonyl-CH₂C(O)-group (keto form) may undergo tautomerism to form ahydroxyl-CH═C(OH)-group (enol form). During application, the compoundalso includes the keto form and enol form alone and mixtures thereof.

The term “acceptable salt” refers to a salt with known cations or aions,and may be applied to form use in the field.

Suitable salts with bases, for example, salts formed from compounds offormula (I) and formula (II) containing carboxyl groups, include saltsof alkali metals (such as sodium and potassium), alkali earth metals(such as calcium and magnesium), ammonium and amines.

Suitable salts with acid radical additives, such as salts formed fromcompounds of formula (I) and formula (II) containing amino, includesalts formed with inorganic acids such as hydrochloride, sulphate,sulphite, phosphate, hydrogen phosphate and nitrate, and salts formedwith organic acids such as acetic acid, malic acid, tartaric acid,citric acid, lactic acid, salicylic acid, oxalic acid, etc.

Moreover, if the compound is obtained as an acid addition salt, freealkalis can be obtained by alkalizing a solution of the acid salt. Incontrast, if a product is a free alkali, the addition salt can beprepared by dissolving the free alkali in a suitable organic solvent andtreating the solution with an acid, which is consistent with aconventional process of preparing an acid addition salt from an alkalinecompound. Those skilled in the art should understand various synthesismethods that can be used to prepare agromedically acceptable additionsalts without undue experimentation.

The compound of the present invention can be used to control and killvarious agroforestry pests, sanitary insect pests and pests harmful toanimal health. In this specification, the “insecticide” is a generaldesignation of substances that have the effect of preventing andcontrolling all the pests mentioned above. Examples of the pestsinclude, but are not limited to: coleoptera insects such as Sitophiluszeamais, Tribolium castaneum, Henosepilachna vigintioctomacta,Henosepilachna sparsa, Agrarius fusillis, Anomala cupripes, Popilliaquadriguttata, Monolepta hieroglyphica, Monochamus alternatus,Echinocnemus squameus, Basiprionota bisignata, Anoplophora chinensis,Apripona germari, Soclytus schevy, or Agriotes fuscicollis; lepidopterainsects such as Lymantria dispar, Malacosoma neustria testacea,Diaphania perspectalis, Clania variegata, Cnidocampa flauescens,Dendrolimus punctatus, Orgyia antiqua, Paranthrene tabaniformis,Spodoptera litura, Chilo suppressalis, Ostrinia nubilalis, Ephestiacautella, Adoxophyes orana, Laspyresia splendana, Agrotis fucosa,Galleria mellonella, Plutella xylostella, Phyllocnistis citrella, orMythimna separata; hemiptera insects such as Stephanitis nashi;homoptera insects such as Nephotettix cincticeps, Unaspis yanonensis,Myzus persicae, Aphis gossydii, or Bemisia tabaci; orthoptera insectssuch as Gryllotalpa africana, or Locus migratoria; hymenoptera insectssuch as Solenopsis invicta, or Tremex fuscicornis; blattaria insectssuch as Blattella germanica, Periplaneta american, or Copotermesformosamus; diptera insects such as Musca domestica, Aedes aegypti,Delia platura, Culex sp., or Anopheles sinensis; and plant parasiticnematodes such as Meloidogyne, Pratylenchus spp., Aphelenchoides besseyiChristie, Bursaphelenchus xylophilus, etc. The pests harmful to animalhealth include Boophilus microplus, Haemaphysalis longicornis, Hyalommaanatolicum, Hypoderma spp., Fasciola hepatica, Moniezia blanchard,Ostertagia spp., Trypanosoma enansi, Babesia bigemina, etc.

The compound related to the present invention preferably has a highactivity on agroforestry pests such as lepidoptera, hymenoptera,hemiptera, coleoptera, diptera and blattaria pests, as well as animalparasitic fleas and/or ticks and mites and sanitary insect pest, andmore preferably has a high activity on piercing-sucking or chewingmouthpart pests.

Insecticide composition containing the active substances of the presentinvention

The active substances of the present invention may be prepared into aninsecticide composition by a conventional method. These active compoundsmay be combined into conventional preparations, such as solutions,emulsions, suspensions, powders, foams, pastes, granules, aerosols,natural and synthetic materials impregnated with the active substances,microcapsules in polymers, coating compounds for seeds, and preparationsfor use with firing units (such as smoking cartridges, smoking cans, andsmoking pans), as well as ultra-low volume (ULV) Cloud mist and Warmmist preparations.

These preparations may be produced by known methods, for example, theactive compounds are mixed with extenders, which are liquid or liquefiedgas or solid diluents or carriers, and optionally surfactants, i.e.,emulsifiers and/or dispersants and/or foam formers. For example, whenwater is used as the extender, organic solvents may also be used asauxiliaries.

It is basically suitable to use liquid solvents as the diluents orcarriers, such as aromatic hydrocarbons, for example, xylene, toluene oralkyl naphthalene; chlorinated aromatic or chlorinated aliphatichydrocarbons such as chlorobenzene, vinyl chloride or methylenechloride; aliphatic hydrocarbons such as cyclohexane, paraffin ormineral oil fractions; alcohols such as ethanol or glycol as well asethers and lipids thereof; ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone; or polar solvents that are notfrequently used such as dimethylformamide, dimethyl sulphoxide, andwater. The liquefied gas diluents or carriers refer to liquids that willbecome gas at normal temperature and pressure, such as aerosolpropellants, for example, halogenated hydrocarbons and butane, propane,nitrogen and carbon dioxide.

The solid carriers may be ground natural minerals such as kaolin, clay,tale, quartz, activated clay, montmorillonite, or diatomite, and groundsynthetic minerals such as highly dispersed silicic acid, alumina, andsilicates. The solid carriers for granules are crushed and gradednatural zircon, such as calcite, marble, pumice, sepiolite and dolomite,as well as granules synthesized from inorganic and organic coarsepowders, and organic materials such as granules of sawdust, coconutshells, corn cobs and tobacco stems, etc.

Non-ionic and anionic emulsifiers may be used as emulsifiers and/or foamformers, for example, polyoxyethylene-fatty acid esters,polyoxyethylene-fatty alcohol ethers, such as alkaryl polyethyleneglycol ethers, alkyl sulfonic acid esters, alkyl sulfates, aryl sulfonicesters, and albumin hydrolysates. The dispersants include, for example,lignin sulfite lye and methylcelluloses.

Adhesives such as carboxymethyl cellulose and natural and syntheticpolymers in the form of powders, granules or emulsions, such as Arabicgum, polyvinyl alcohol and polyvinyl acetate, may be used in thepreparations. Colorants such as inorganic fuels, for example, ironoxide, cobalt oxide and Prussian blue; organic dyes, such as dichlorodyes or metal cyanine dyes; and trace nutrients such as salts of iron,manganese, boron, cop, cobalt, aluminum and zinc may be used.

These active compounds of the present invention may be mixed with otheractive compounds to prepare a mixture that can be present in commercialpreparations or in use preparation forms prepared from thesepreparations. The other active compounds include, but are not limitedto: insecticides, baits, fungicides, acaricides, nematicides,fungicides, growth control agents, and the like. The insecticidesinclude, for example, phosphates, carbamates, pyrethroids, chlorinatedhydrocarbons, benzamides, nereistoxin and substances produced bymicroorganisms, such as abamectin.

Furthermore, these active compounds of the present invention may also bemixed with synergists to prepare a mixture that can be present incommercial preparations or in use preparation forms prepared from thesepreparations. The synergist is a compound that enhances the effect ofthe active compounds. Since the active compounds have activity, it isnot necessary to add the synergist.

These preparations generally contain 0.001 to 99.99% by weight,preferably 0.01 to 99.9% by weight, more preferably 0.05 to 90% byweight of the active compound of the present invention in theinsecticide composition. Concentration of the active compounds in theuse preparation form prepared from the commercial preparations may varywithin a wide range. The concentrations of the active compounds in theuse preparation forms may range from 0.0000001 to 100% (g/v), and maypreferably be between 0.0001 and 1%.

The present invention will be described in further detail below withreference to the specific embodiments, and the specific embodiments areonly used to explain the present invention and are not used to limit thescope of the present invention. The experimental methods used in thefollowing embodiments are conventional unless otherwise specified. Thematerials and reagents used are commercially available materials andreagents unless otherwise specified.

SYNTHESIS EMBODIMENTS Embodiment 1: Synthesis of Compounds A1 to A47 byUsing a Method A

For instance, synthesis of a compound A1:

S1:5-amino-1H-pyrazole-3-cyano

Ethyl 2,3-dicyanopropionate (1.0 mmol) was added to 20.0 ml of ethanoland stirred vigorously, then hydrazine hydrate (2.0 mmol) was added tothe reaction solution, heated and refluxed, then the heating was stoppedafter 3 hours, and the mixture was cooled to room temperature. Themixture was concentrated in vacuum and extracted with ethyl acetate andwater, then the obtained ethyl acetate was concentrated and extracted invacuum to obtain white solid 5-amino-1H-pyrazole-3-cyano, and theintermediate was directly used for next step without furtherpurification.

S2:5,5-dimethyl-4,5-dihydropyrazole[1,5-α]quinazoline-2-cyano

Under the protection of nitrogen, a DMF mixture of5-amino-H-pyrazole-3-cyano (1.0 mmol),1-bromo-2-(1-bromo-1-methylethyl)benzene (1.0 mmol), cuprous iodide (0.2mmol) and cesium carbonate (0.5 mmol) was stirred at 100° C. for 24hours. The mixture was cooled to room temperature, and then filtered,and concentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound5,5-dimethyl-4,5-dihydropyrazole[1,5-α]quinazoline-2-cyano (yield of thetwo steps: 45%).

The compounds A2 to A47 were synthesized with reference to the method ofthe compound A1 (wherein cyclization steps also included similarcyclization methods mentioned in documents such as Tetrahedron Letters(2015) 56: 1367; WO2016046404, and WO2013174822), with a difference thatdifferent raw materials were selected for reaction according todifferent target compounds, or the compounds were derived from thesynthesized target products. Specific compounds were as shown in Table1:

TABLE 1 Com- pound Structural formula R¹¹ R¹² R¹³ R¹⁴ R¹⁵ R¹⁶ A1

—CN —H —H —CH₃ —CH₃ —H A2

—CN —Br —H —CH₃ —CH₃ —H A3

—CN —Br —CH₃ —CH₃ —CH₃ —H A4

—CN —Br —Ac —CH₃ —CH₃ —H A5

—Ac —Br —H —CH₃ —CH₃ —H A6

—CONHCH₃ —Br —H —CH₃ —CH₃ —H A7

—CONC₅H₁₀ —Br —H —CH₃ —CH₃ —H A8

—CN —SOCF₃ —H —CH₃ —CH₃ —H A9

—CN —SC₂H₅ —H —CH₃ —CH₃ —H A10

—CF₃ —H —H —CF₃ —CF₃ 5′-NH₂ A11

—CF₃ -Br -H —CF₃ —CF₃ 5'-NH₂ A12

—CF₃ -4 fluorophenyl —H —CF₃ —CF₃ 5'-NH₂ A13

—CF₃ —SCF₃ —H —CF₃ —CF₃ 5′-NH₂ A14

—CF₃ —SOC₂H₅ —H —CF₃ —CF₃ 5′-NH₂ A15

—CN —NH₂ —H —CH₃ —CH₃ —H A16

—CN —NHC₄H₉ —H —CH₃ —CH₃ —H A17

—CN —NHCOCH₃ —H —CH₃ —CH₃ —H A18

—CN —NHCO₂Ph —H —CH₃ —CH₃ —H A19

—CN —NHCONHCH₃ —H —CH₃ —CH₃ —H A20

—CN —NHSO₂Ph-4CH₃ —H —CH₃ —CH₃ —H A21

—CN —NO₂ —H —CH₃ —CH₃ —H A22

—H —CN —H —CH₂NH₂ —F 5-Cl A23

—H —CN —H —CH₂NH₂ —NH₂ 5-Cl A24

—H —CN —H —CH₂NHCH₃ —NHCH₃ 5-Cl A25

—SCH₃ —CN —H —CF₃ —F / A26

—SOCH₃ —CN —H —CF₃ —F / A27

—SCH₃ —COOEt —H —CF₃ —F / A28

—SCH₃ —CONH₂ —H —CF₃ —F / A29

—SCH₃ —CON(CH₃)₂ —H —CF₃ —F / A30

—SCH₃ —CON₂C₄CH₃ —H —CF₃ —F / A31

—SCH₃ —CN —COOPh —CF₃ —F / A32

—SCH₃ —CN —CONHCH₃ —CF₃ —F / A33

—SCH₃ —CN —SO₂CH₃ —CF₃ —F / A34

—SCH₃ —CN —CH₂C₂H₃ —CF₃ —F / A35

—SCH₃ —CN —C₂H₄Br —CF₃ —F / A36

—NH₂ —H —H CH₂CF₃ —F Z²═N A37

—NHC₂H₅ —H —H —CH₂CF₃ —F Z²═N A38

—N(C₂H₅)CH₂C₂H₃ —H —H —CH₂CF₃ —F Z²═N A39

—NHCOCH₃ —H —H —CH₂CF₃ —F Z²═N A40

—NHCOOCH₃ —H —H —CH₂CF₃ —F Z²═N A41

—NHCONHCH₃ —H —H —CH₂CF₃ —F Z²═N A42

—NHSO₂CH₃ —H —H —CH₂CF₃ —F Z²═N A43

—NO₂ —H —H —CH₂CF₃ —F Z²═N A44

—SCH₃ —COOEt —H —CH₃ —CH₃ 4-F, Z²═Z⁴═N A45

—SCH₃ —SO₂Ph —H —CH₃ —CH₃ 4-F, Z²═Z⁴═N A46

—SCH₂Ph —CN —H —CH₃ —CH₃ 4-F, Z²═Z⁴═N A47

—SO₂CH₂Ph —CN —H —CH₃ —CH₃ 4-F, Z²═Z⁴═N

Embodiment 2: Synthesis of Compounds B1 to B12 by Using a Method B

For instance, synthesis of a compound B1:

S1:2-amino-4-(4-methoxybenzene)-1H-pyrrole-3-cyano

2-bromo-1-(4-methoxyphenyl)-acetyl (1.0 mmol) was added to 15 ml of DMF,and then sodium azide (10.0 mmol) was added to the reaction solution.After the reaction mixture was stirred for 48 hours, the reactionmixture was filtered, and an obtained filtrate was extracted with ethylether for multiple times. Concentration in vacuum was performed, theresidues were dissolved with methanol, and then 10% palladium carbon(0.2 mmol) was added thereto in a hydrogen atmosphere. The reactionmixture was stirred for 24 hours, and then filtered. An obtainedfiltrate was concentrated in vacuum, the residues were dissolved withtetrahydrofuran, and then acetic anhydride (2.0 mmol) and triethylamine(2.0 mmol) were added thereto. The reaction mixture was stirred for 5hours, and then concentrated in vacuum, and the residues were purifiedby column chromatography to obtainN-(2-(4-methoxyphenyl)-2-ethoxy)-acetamide (yield: 78%).

N-(2-(4-methoxyphenyl)-2-ethoxy)-acetamide (1.0 mmol) was added to 15 mlof ethanol, and then malononitrile (2.0 mmol) and sodium ethoxide (1.5mmol) were added thereto. The mixture was heated and refluxed for 12hours, and then concentrated in vacuum, and the residues were purifiedby column chromatography to obtain the target compound (yield: 89%).

S2:2-bromo-2-(2-chloro-4-nitrophenyl)malononitrile

Under nitrogen protection, 2-chloro-4-nitro-benzoyl chloride (1.0 mmol)was dissolved in 10 ml of dry pyridine, cooled to 0° C., thentrimethylsilylnitrile (1.1 mmol) was slowly added dropwise to thereaction solution, and the reaction solution was naturally heated toroom temperature. After stirring for 10 hours, the reaction mixture wascooled to 0° C. again, and 2 ml of phosphorous oxybromide was added tothe reaction mixture. After stirring for 12 hours, the solution wasremoved in vacuum, and the residues were extracted with water and ethylacetate. Then the ethyl acetate was obtained by concentration andextraction in vacuum, and the residues were purified by columnchromatography to obtain the2-bromo-2-(2-chloro-4-nitrophenyl)malononitrile (yield: 56%).

S3:2-(4-methoxybenzene)-8-nitropyrrole[1,2-α]quinazoline-3,5,5(4H)-tricyano

Under the protection of nitrogen, a DMF mixture of2-amino-4-(4-methoxybenzene)-1H-pyrrole-3-cyano (1.0 mmol),2-bromo-2-(2-chloro-4-nitrophenyl)malononitrile (1.1 mmol), cuprousiodide (0.2 mmol) and sodium ethoxide (0.5 mmol) was stirred at 120° C.for 24 hours. The mixture was cooled to room temperature, and thenfiltered, and concentrated in vacuum, and the residues were purified bycolumn chromatography to obtain the2-(4-methoxybenzene)-8-nitropyrrole[1,2-α]quinazoline-3,5,5(4H)-tricyano(yield: 53%).

The compounds B2 to B12 were synthesized with reference to the method ofthe compound B1 (similar cyclization methods mentioned in documents suchas Synthetic Communications (2015) 45: 2426; Tetrahedron (2014) 55:4997; and WO2007149907), with a difference that different raw materialswere selected for reaction according to different target compounds, andsome compounds, such as compounds B9, B10, B11, B12, etc., could beobtained by modifying B7. Specific compounds were as shown in Table 2:

TABLE 2 Compound Structural formula R¹¹ R¹² R¹³ R¹⁴ R¹⁵ R¹⁶ B1

4-methoxy phenyl —CN —H —CN —CN 5′-NO₂ B2

4- methoxy phenyl —CN —CH₃ —CN —CN 5′-NO₂ B3

4- methoxy phenyl —COCH₃ —H —CN —CN 5′-NO₂ B4

4- methoxy phenyl —COCH₃ —H —CONH₂ —CONH₂ 5′-NO₂ B5

Phenyl —SO₂Ph —H —F —F 5′-Cl B6

—CN —CN —H —CN —CN 5′-NO₂ B7

—CN —CN —H —CN —CN 5′-NH₂ B8

—CN —CN —H —CN —CN 5′- NHCOC₂ H₃ B9

—CN —CN —H —CN —CN 5′-Br B10

—CN —CN —H —CN —CN 5′- NHSO₂C H₃ B11

—CN —CN —H —CN —CN 5′- NHCOOC H₃ B12

—CN —CN —H —CN —CN 5′- NHCONH CH₃

Embodiment 3: Synthesis of Compounds C1 to C64 by Using a Method C

For instance, synthesis of a compound C1:

S1: (2-amino-3-chloro-5-(trifluoromethyl)phenyl)boric acid

Under the protection of nitrogen,2-bromo-6-chloro-4-trifluoromethylaniline (1.0 mmol) was dissolved in 20ml of dry tetrahydrofuran, and cooled to 0° C., then n-butyl lithium(2.5 mmol, 1.6 M n-hexane solution) was slowly added dropwise to thereaction mixture, and stirred for 2 hours. Trimethylchlorosilane (2.5mmol) was slowly added dropwise to the reaction mixture for reaction,and then the reaction mixture was naturally heated and stirred for 12hours, the solvent was removed by vacuum concentration, and the targetcompound (2-amino-3-chloro-5-(trifluoromethyl)phenyl)boric acid (yield:87%) was obtained by reduced pressure distillation.

S2:2-chloro-6-(1,2-dichloro-3-butene-2-yl)-4-(trifluoromethyl)phenylamine

Under the protection of nitrogen, a DMF mixture (3.0 ml) of3-bromo-3,4-dichloro-1-butene (1.0 mmol), Pd(dppf)Cl₂ (0.15 mmol),sodium carbonate (0.15 mmol) and(2-amino-3-chloro-5-(trifluoromethyl)phenyl)boric acid (1.5 mmol) andwater (0.5 ml) were stirred at 100° C. for 10 hours. After the solutionwas removed in vacuum, the residues were diluted with water (10 ml).Then a water layer was extracted with ethyl acetate, and the ethylacetate was obtained by concentration and extraction in vacuum, and theresidues were purified by column chromatography to obtain the targetcompound2-chloro-6-(1,2-dichloro-3-butene-2-yl)-4-(trifluoromethyl)phenylamine(yield: 85%).

S3:2-bromo-1-chloro-3-(1,2-dichloro-3-butene-2-yl)-5-(trifluoromethyl)phenyl

Under the protection of nitrogen,2-bromo-1-chloro-3-(1,2-dichloro-3-butene-2-yl)-5-(trifluoromethyl)phenyl(1.0 mmol) and cupric bromide (1.5 mmol) were dissolved in 10 ml ofacetonitrile, cooled to −5° C., and then isoamyl nitrite (1.3 mmol) wasslowly added thereto, and the reaction mixture was heated to 50° C.After three hours, the mixture was filtered, and the filtrate wasconcentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound2-bromo-1-chloro-3-(1,2-dichloro-3-butene-2-yl)-5-(trifluoromethyl)phenyl(yield: 91%).

S4:9-chloro-7-trifluoromethylphenyl-5-chloromethyl-5-vinyl-4,5-dihydropyrrole[1,5-α]quinazoline-2-cyano

Under the protection of nitrogen, a DMF mixture of5-amino-1H-pyrazole-3-cyano (1.0 mmol),2-bromo-1-chloro-3-(1,2-dichloro-3-butene-2-yl)-5-(trifluoromethyl)phenyl(1.1 mmol), cuprous iodide (0.2 mmol) and sodium ethoxide (0.5 mmol) wasstirred at 120° C. for 24 hours. The mixture was cooled to roomtemperature, and then filtered. The filtrate was concentrated in vacuum,and the residues were purified by column chromatography to obtain thetarget compound9-chloro-7-trifluoromethylphenyl-5-chloromethyl-5-vinyl-4,5-dihydropyrrole[1,5-α]quinazoline-2-cyano(yield: 52%).

The compounds C2 to C64 were synthesized with reference to the method ofthe compound C1 (similar cyclization methods were mentioned in documentssuch as WO2007144669), with a difference that different raw materialswere selected for reaction according to different target compounds.Specific compounds were as shown in Table 3.

TABLE 3 Compound Structural formula R¹¹ R¹² R¹³ R¹⁴ R¹⁵ R¹⁶ C1

—CN —H —H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C2

—CN —H —H —C₂H₃ —CH₂CF₃ 4′-CF₃, 6′-Cl C3

—CN —H —H —C₂H₃ —CF₃ 4′-CF₃, 6′-Cl C4

—CN —H —H —C₂H₃ —H 4′-CF₃, 6′-Cl C5

—CN —Br —H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C6

—CN —Br —H —C₂H₃ —CH₂CF₃ 4′-CF₃, 6′-Cl C7

—CN —Br —H —C₂H₃ —CF₃ 4′-CF₃, 6′-Cl C8

—CN —Br —H —C₂H₃ —H 4′-CF₃, 6′-Cl C9

—CN -6 trifluoro methylphenyl [*]—H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C10

—CN -3-2,5- dimethyl furanyl —H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C11

—CN -6 trifluoro methylphenyl —H —C₂H₃ —CF₃ 4′-CF₃, 6′-Cl C12

—CN -3-2,5- dimethyl furanyl —H —C₂H₃ —CF₃ 4′-CF₃, 6′-Cl C13

—CN —SOCF₃ —H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C14

—CN —SOCF₃ —H —C₂H₃ —CH₂CF₃ 4′-CF₃, 6′-Cl C15

—CN —SOCF₃ —H —C₂H₃ —CF₃ 4′-CF₃, 6′-Cl C16

—CN —SOCF₃ —H —C₂H₃ —CH 4′-CF₃, 6′-Cl C17

—CN —SOC₂H₅ —H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C18

—CN —SOCH₃ —H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C19

—COCH₃ —SOCH₃ —H —C₂H₃ —CH₂Cl 4′-CF₃, 6′-Cl C20

—CN —SOCF₃ —H —C₂H₃ —CH₂CN 4′-CF₃, 6′-Cl C21

—CN —SOC₂H₅ —H —C₂H₃ —CH₂CN 4′-CF₃, 6′-Cl C22

—CN —SOCH₃ —H —C₂H₃ —CH₂CN 4′-CF₃, 6′-Cl C23

—COCH3 —SOC₂H₅ —H —C₂H₃ —CH₂CN 4′-CF₃, 6′-Cl C24

—CN —SOCF₃ —H —CH₂CN —CH₂OH 4′-CF₃, 6′-Cl C25

—CN —SOC₂H₅ —H —CH₂CN —CH₂OH 4′-CF₃, 6′-Cl C26

—CN —SOCH₃ —H —CH₂CN —CH₂OH 4′-CF₃, 6′-Cl C27

—COCH₃ —SOCH₃ —H —CH₂CN —CH₂OH 4′-CF₃, 6′-Cl C28

—CN —SOCF₃ —H —CH₂CN —CH₂Br 4′-CF₃, 6′-Cl C29

—CN —SOCF₃ —H —CH₂CN —CH₂N(CH₃)₂ 4′-CF₃, 6′-Cl C30

—CN —SOCF₃ —H —CH₂CN —COOH 4′-CF₃, 6′-Cl C31

—CN —SOCF₃ —H —CH₂CN —COOMe 4′-CF₃, 6′-Cl C32

—CN —SOCF₃ —H —CH₂CN —CONH₂ 4′-CF₃, 6′-Cl C33

—CN —SOCF₃ —H —CH₂CN —CONHCH₃ 4′-CF₃, 6′-Cl C34

—CN —SOCF₃ —H —CH₂CN —CON₂C₄CH₃ 4′-CF₃, 6′-Cl C35

—CN —SOCF₃ —H —CH₂COMe —CONHCH₃ 4′-CF₃, 6′-Cl C36

—CN —SOCF₃ —H —CH₂COOH —COOH 4′-CF₃, 6′-Cl C37

—CN —SOCF₃ —H —CH₂COOH —COOMe 4′-CF₃, 6′-Cl C38

—CN —SOCF₃ —H —CH₂COONH₂ —COONH₂ 4′-CF₃, 6′-Cl C39

—CN —SOCF₃ —H —CH₂COMe —COOMe 4′-CF₃, 6′-Cl C40

—CN —SOCF₃ —COCH₃ —CH₂COOMe —COOMe 4′-CF₃, 6′-Cl C41

—COCH₃ —SOCH₃ —H —CH₂CN —CH₂Br 4′-CF₃, 6′-Cl C42

—COCH₃ —SOCH₃  H —CH₂NHCH₃ —CH₂CN 4′-CF₃, 6′-Cl C43

—COCH₃ —SOCH₃  H —COOH —CH₂CN 4′-CF₃, 6′-Cl C44

—COCH₃ —SOCH₃ —H —COOMe —CH₂CN 4′-CF₃, 6′-Cl C45

—COCH₃ —SOCH₃  H —CONHCH₃ —CH₂CN 4′-CF₃, 6′-Cl C46

—COCH₃ —SOCH₃ —H —CONHCH₃ —CH₂COOMe 4′-CF₃, 6′-Cl C47

—COCH₃ —SOCH₃ —H —COOH —CH₂COOH 4′-CF₃, 6′-Cl C48

—COCH₃ —SOCH₃ —H —COOME —CH₂COOMe 4′-CF₃, 6′-Cl C49

—COCH₃ —SOCH₃ —H —CONH₂ —CH₂CONH₂ 4′-CF₃, 6′-Cl C50

—CN -3-2,5- dimethyl furanyl —H —C₂H₃ —H 4′-CF₃, 6′-Cl C51

—CN —SOCF₃ —H —C₂H₃(OH)₂ —H 4′-CF₃, 6′-Cl C52

—CN -3-2,5- dimethyl furanyl —H —C₂H₃(OH)₂ —H 4′-CF₃, 6′-Cl C53

—CN 6- trifluoro methylphenyl —H —C₂H₃(OH)₂ —CH₂Cl 4′-CF₃, 6′-Cl C54

—CN -3-2,5- dimethyl furanyl —H —C₂H₃(OH)₂ —CF₃ 4′-CF₃, 6′-Cl C55

—CN —SOCF₃ —H —C₂H₃(OH)₂ —CH₂Cl 4′-CF₃, 6′-Cl C56

—CN —SOCF₃  H —C₂H₃(OH)₂ —CH₂CF₃ 4′-CF₃, 6′-Cl C57

—CN —SOCF₃  H —C₂H₃(OH)₂ —CF₃ 4′-CF₃, 6′-Cl C58

—CN —SOCF₃ —H —CH₂CN —C₂H₂COOMe 4′-CF₃, 6′-Cl C59

—CN —SOC₂H₅ —H —CH₂CN —C₂H₂COOMe 4′-CF₃, 6′-Cl C60

—COCH₃ —SOCH₃ —H —CH₂CN —C₂H₂COOMe 4′-CF₃, 6′-Cl C61

—C₂H₅ —Br —H —C₂H₃ —C₂H₃ 4′-CF₃, 6′-Cl C62

—C₂H₅ -3-2,5- dimethyl thienyl —H —C₂H₃ —C₂H₃ 4′-CF₃, 6′-Cl C63

—C₂H₅ —Br —H —C₂H₂COOMe —C₂H₂COOMe 4′-CF₃, 6′-Cl C64

—C₂H₅ -3-2,5- dimethyl thienyl —H —C₂H₂COOMe —C₂H₂COOMe 4′-CF₃, 6′-Cl

TABLE 4 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance of Some Compounds shown in Formula (I) of Table 1 Com- pound¹H-NMR(600 MHz) MS (ESI) A1 ¹H-NMR (600 MHz, CDCl₃) δ 7.73 [M + H]⁺225.1 (dd, J = 8.0, 1.4 Hz, 1H), 7.50-7.46 (m, 1H), 7.44-7.37 (m, 2H),5.93 (s, 1H), 5.78 (Brs, 1H), 1.27(s, 3H), 1.25(s, 3H). A2 ¹H-NMR (600MHz, CDCl₃) δ 7.75 [M + H]⁺ 302.9 (dd, J = 8.0, 1.3 Hz, 1H), 7.56-7.51(m, 1H), 7.48-7.45 (m, 2H), 5.86 (Brs, 1H), 1.28(s, 3H), 1.27(s, 3H). A4¹H-NMR (600 MHz, CDCl₃) δ 7.75 [M + H]⁺ 345.1 (dd, J = 8.0, 1.3 Hz, 1H),7.56-7.51 (m, 1H), 7.48-7.45 (m, 2H), 2.06 (s, 3H), 1.30(s, 3H), 1.29(s,3H). A5 ¹H-NMR (600 MHz, CDCl₃) δ 7.77 [M + H]⁺ 319.8 (dd, J = 8.0, 1.3Hz, 1H), 7.57-7.53 (m, 1H), 7.49-7.47 (m, 2H), 2.16 (s, 3H), 1.28(s,3H), 1.27(s, 3H). A7 ¹H-NMR (600 MHz, CDCl₃) δ 7.77 [M + H]⁺ 389.3 (dd,J = 8.0, 1.3 Hz, 1H), 7.57-7.53 (m, 1H), 7.49-7.47 (m, 2H), 2.01-1.93(m, 2H), 1.83-1.74 (m, 2H), 1.67-1.59 (m, 1H), 1.40-1.27 (m, 4H),1.28(s, 3H), 1.27(s, 3H) , 1.24- 1.13 (m, 1H). A8 ¹H-NMR (600 MHz,CDCl₃) δ 7.78 (dd, [M + H]⁺ 341.0 J = 8.0, 1.3 Hz, 1H), 7.58-7.54 (m,1H), 7.50-7.48 (m, 2H), 5.86 (Brs, 1H), 1.28(s, 3H), 1.27(s, 3H). A12¹H-NMR (600 MHz, CDCl₃) δ 7.40-7.38 [M + H]⁺ 485.4 (m, 2H), 7.35-7.33(m, 2H), 7.12 (d, J = 8.0, 2H), 6.68-6.65 (m, 1H), 6.63-6.61 (m, 1H),5.86 (Brs, 1H), 5.78 (s, 1H). A15 ¹H-NMR (600 MHz, CDCl₃) δ 7.73 [M +H]⁺ 240.5 (dd, J = 8.0, 1.4 Hz, 1H), 7.50-7.46 (m, 1H), 7.44-7.37 (m,2H), 6.26 (Brs, 2H), 5.78 (Brs, 1H), 1.27(s, 3H), 1.25(s, 3H). A18¹H-NMR (600 MHz, CDCl₃) δ 9.25 [M + H]⁺ 359.9 (Brs, 1H), 7.73 (dd, J =8.0, 1.4 Hz, 1H), 7.50-7.46 (m, 1H), 7.44-7.37 (m, 2H), 7.27-7.19 (m,3H), 7.14- 7.10 (m, 2H), 5.58 (Brs, 1H), 1.27(s, 3H), 1.25(s, 3H). A19¹H-NMR (600 MHz, CDCl₃) δ 7.73 [M + H]⁺ 297.4 (dd, J = 8.0, 1.4 Hz, 1H),7.50-7.46 (m, 1H), 7.44-7.37 (m, 2H), 6.06 (s, 1H), 5.78 (Brs, 1H),2.78(s, 3H), 1.29(s, 3H), 1.28(s, 3H). A21 ¹H-NMR (600 MHz, CDCl₃) δ7.76 (dd, [M + H]⁺ 270.3 J = 8.0, 1.3 Hz, 1H), 7.56-7.51 (m, 1H),7.49-7.47 (m, 2H), 5.93 (Brs, 1H), 1.29(s, 3H), 1.27(s, 3H). A22 ¹H-NMR(600 MHz, CDCl₃) δ 8.30 [M + H]⁺ 278.2 (s, 1H), 8.17 (d, J = 7.6 Hz,1H), 8.10- 8.08 (m, 1H), 7.46 (d, J = 2.5 Hz, 1H), 5.21 (s, 1H), 4.78(brs, 2H), 3.21- 3.45(m, 2H). A26 ¹H-NMR (600 MHz, CDCl₃) δ 7.78 [M +H]⁺ 345.1 (dd, J = 8.0, 1.3 Hz, 1H), 7.58-7.54 (m, 1H), 7.50-7.48 (m,2H), 5.86 (Brs, 1H), 3.06 (s, 3H). A27 ¹H-NMR (600 MHz, CDCl₃) δ 7.79[M + H]⁺ 376.0 (dd, J = 8.0, 1.3 Hz, 1H), 7.57-7.54 (m, 1H), 7.49-7.48(m, 2H), 5.5 (Brs, 1H), 4.38 (d, J = 7.3 Hz, 2H), 2.54 (s, 3H), 1.29 (t,J = 7.3 Hz, 3H). A29 ¹H-NMR (600 MHz, CDCl₃) δ 7.79 [M + H]⁺ 375.1 (dd,J = 8.0, 1.3 Hz, 1H), 7.57-7.54 (m, 1H), 7.49-7.48 (m, 2H), 5.5 (Brs,1H), 2.93 (s, 6H) 2.54 (s, 3H). A33 ¹H-NMR (600 MHz, CDCl₃) δ 7.79 [M +H]⁺ 407.1 (dd, J = 8.0, 1.3 Hz, 1H), 7.57-7.54 (m, 1H), 7.49-7.48 (m,2H), 5.5 (Brs, 1H), 3.35 (s, 3H) 2.56 (s, 3H). A37 ¹H-NMR (600 MHz,CDCl₃) δ 8.40 [M + H]⁺ 316.1 (s, 1H), 7.50-7.46 (m, 1H), 7.44- 7.37 (m,1H), 6.56 (s, 1H), 5.78 (Brs, 1H), 4.56 (s, 1H), 4.38 (d, J = 7.3 Hz,2H), 2.56-2.58(m, 2H), 1.29 (t, J = 7.3 Hz, 3H). A43 ¹H-NMR (600 MHz,CDCl₃) δ 8.41 [M + H]⁺ 318.1 (s, 1H), 7.50-7.46 (m, 1H), 7.44- 7.37 (m,1H), 6.76 (s, 1H), 5.78 (Brs, 1H), 2.56-2.58(m, 2H). A44 ¹H NMR (600MHz, CDCl₃) δ 9.18 [M + H]⁺ 338.3 (s, 1H), 5.78 (Brs, 1H), 4.35 (d, J =7.3 Hz, 2H), 2.54(s, 3H), 1.28 (t, J = 7.3 Hz, 3H), 1.27 (s, 3H), 1.26(s, 3H). A45 ¹H-NMR (600 MHz, CDCl₃) δ 9.18 [M + H]⁺ 405.1 (s, 1H),7.44-7.37 (m, 2H), 7.27- 7.19 (m, 3H), 5.78 (Brs, 1H), 2.54(s, 3H), 1.27(s, 3H), 1.26 (s, 3H). A46 ¹H-NMR (600 MHz, CDCl₃) δ 9.20 [M + H]⁺ 367.0(s, 1H), 7.44-7.37 (m, 2H), 7.27- 7.19 (m, 3H), 5.78 (Brs, 1H),4.46-4.44 (m, 2H), 1.27 (s, 3H), 1.26 (s, 3H).

TABLE 5 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance of Some Compounds shown in Formula (I) of Table 2 Com- pound¹H-NMR (600 MHz) MS (ESI) B1 ¹H NMR (600 MHz, CDCl₃) δ 8.19 [M + H]⁺397.1 (d, J = 7.6 Hz, 1H), 8.11 (d, J = 8.0 Hz, 1H), 7.68 (d, J = 3.6Hz, 2H), 7.48 (d, J = 2.6 Hz, 1H), 7.25 (s, 1H), 7.15 (d, J = 3.8 Hz,2H), 5.40 (s, 1H), 3.86 (s, 3H). B4 ¹H NMR (600 MHz, DMSO) δ 8.21 [M +H]⁺ 450.3 (d, J = 7.6 Hz, 1H), 8.15 (d, J = 8.0 Hz, 1H), 7.78 (d, J =3.6 Hz, 2H), 7.53 (d, J = 2.6 Hz, 1H), 7.33 (s, 1H), 7.18 (d, J = 3.8Hz, 2H), 6.67 (brs, 2H), 6.43 (brs, 2H), 5.44 (s, 1H), 3.89 (s, 3H),2.59 (s, 3H). B5 ¹H NMR (600 MHz, CDCl₃) δ 7.87 (d, [M + H]⁺ 469.9 J =7.6 Hz, 2H), 7.69-7.68 (m, 1H), 7.68 (d, J = 3.6 Hz, 2H), 7.51-7.50 (m,2H), 7.42-7.40 (m, 2H), 7.41-7.40 (m, 1H), 7.31-7.30 (m, 1H), 7.25 (s,1H), 7.15-7.14 (m, 1H), 5.40 (s, 1H), 2.28 (s, 3H). B6 ¹H NMR (600 MHz,CDCl₃) δ 8.18 (d, [M + H]⁺ 316.2 J = 7.6 Hz, 1H), 8.11 (d, J = 8.0 Hz,1H), 7.48 (d, J = 2.6 Hz, 1H), 7.24 (s, 1H), 5.38 (s, 1H). B7 ¹H NMR(600 MHz, CDCl₃) δ 8.18 [M + H]⁺ 286.2 (d, J = 7.6 Hz, 1H), 8.11 (d, J =8.0 Hz, 1H), 7.48 (d, J = 2.6 Hz, 1H), 7.24 (s, 1H), 5.38 (s, 1H), 4.67(brs, 2H). B8 ¹H NMR (600 MHz, CDCl₃) δ 9.76(s, [M + H]⁺ 340.0 1H), 8.17(d, J = 7.6 Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 2.6 Hz, 1H),7.25 (s, 1H), 6.53-6.55 (m, 1H), 6.02 (dd, J = 8.0, 2.0 Hz, 1H), 5.86(dd, J = 6.0, 2.0 Hz, 1H), 5.38 (s, 1H),. B9 ¹H NMR (600 MHz, CDCl₃) δ8.17 [M + H]⁺ 349.1 (d, J = 7.6 Hz, 1H), 8.10 (d, J = 7.9 Hz, 1H), 7.46(d, J = 2.5 Hz, 1H), 7.24 (s, 1H), 5.21 (s, 1H).

TABLE 6 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance Com- pound ¹H-NMR(600 MHz) MS (ESI) C5 ¹H NMR (600 MHz, CDCl₃)δ 8.13 [M + H]⁺ 450.9 (s, 1H), 7.58 (s, 1H), 7.28 (s, 1H), 6.30-6.29 (m,1H), 5.02-4.99 (m, 2H), 3.55-3.23 (m, 2H). C6 ¹H NMR (600 MHz, CDCl₃) δ8.14 [M + H]⁺ 485.1 (s, 1H), 7.56 (s, 1H), 7.17 (s, 1H), 6.30-6.29 (m,1H), 5.02-4.99 (m, 2H), 2.81-2.79 (m, 2H). C7 ¹H NMR (600 MHz, CDCl₃) δ8.13 [M + H]⁺ 470.9 (s, 1H), 7.58 (s, 1H), 7.28 (s, 1H), 6.30-6.29 (m,1H), 5.02-4.99 (m, 2H). C8 ¹H NMR (600 MHz, CDCl₃) δ 8.13 [M + H]⁺ 402.9(s, 1H), 7.58 (s, 1H), 7.28 (s, 1H), 6.30-6.29 (m, 1H), 5.02-4.99 (m,2H), 4.65 (t, J = 3.6 Hz, 1H). C9 ¹H NMR (600 MHz, CDCl₃) δ 8.13 [M +H]⁺ 517.1 (s, 1H), 7.72 (d, J = 7.6 Hz, 1H), 7.68 (d, J = 6.8 Hz, 1H),7.51-7.49 (m, 2H), 7.58 (s, 1H), 7.28 (s, 1H), 6.30- 6.29 (m, 1H),5.02-4.99 (m, 2H), 3.55-3.23 (m, 2H). C12 ¹H NMR (600 MHz, CDCl₃) δ 8.13[M + H]⁺ 487.0 (s, 1H), 7.58 (s, 1H), 7.28 (s, 1H), 6.30-6.29 (m, 1H),6.01 (s, 1H), 5.02-4.99 (m, 2H), 2.28 (s, 3H), 2.25 (s, 3H). C15 ¹H NMR(600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 508.9 (s, 1H), 7.58 (s, 1H), 7.16 (s,1H), 6.30-6.29 (m, 1H), 5.02-4.99 (m, 2H). C20 ¹H NMR (600 MHz, CDCl₃) δ8.14 [M + H]⁺ 480.0 (s, 1H), 7.56 (s, 1H), 7.17 (s, 1H), 6.30-6.29 (m,1H), 5.02-4.99 (m, 2H), 2.86-2.73 (m, 2H). C24 ¹H NMR (600 MHz, CDCl₃) δ8.14 (s, [M + H]⁺ 484.1 1H), 7.56 (s, 1H), 7.11 (s, 1H), 4.56 (s, 1H),2.86-2.73 (m, 2H), 2.64-2.53 (m, 2H). C28 ¹H NMR (600 MHz, CDCl₃) δ 8.15[M + H]⁺ 545.9 (s, 1H), 7.57 (s, 1H), 7.08 (s, 1H), 2.86-2.73 (m, 2H),2.64-2.53 (m, 2H). C30 ¹H NMR (600 MHz, CDCl₃) δ 10.20 [M + H]⁺ 497.9(brs, 1H), 8.14 (s, 1H), 7.56 (s, 1H), 7.11 (s, 1H), 2.86-2.73 (m, 2H).C31 ¹H NMR (600 MHz, CDCl₃) δ 8.14 [M + H]⁺ 511.9 (s, 1H), 7.56 (s, 1H),7.11 (s, 1H), 3.68 (s, 3H), 2.86-2.73 (m, 2H). C36 ¹H NMR (600 MHz,CDCl₃) δ 10.20 [M + H]⁺ 516.9 (brs, 1H), 9.86 (brs, 1H), 8.13 (s, 1H),7.58 (s, 1H), 7.28 (s, 1H), 3.55-3.23 (m, 2H). C37 ¹H NMR (600 MHz,CDCl₃) δ 8.13 [M + H]⁺ 545.0 (s, 1H), 7.58 (s, 1H), 7.28 (s, 1H), 3.82(s, 3H), 3.66 (s, 3H), 3.55-3.23 (m, 2H). C40 ¹H NMR (600 MHz, CDCl₃) δ8.13 [M + H]⁺ 587.0 (s, 1H), 7.58 (s, 1H), 3.82 (s, 3H), 3.66 (s, 3H),3.55-3.23 (m, 2H), 2.04 (s, 3H). C54 ¹H NMR (600 MHz, CDCl₃) δ 8.13 [M +H]⁺ 521.0 (s, 1H), 7.58 (s, 1H), 7.18 (s, 1H), 6.03 (s, 1H), 4.06-4.04(m, 1H) 3.81-3.56 (m, 2H), 3.78 (s, 1H), 3.44 (s, 1H), 2.82 (s, 3H),2.66 (s, 3H),. C59 ¹H NMR (600 MHz, CDCl₃) δ 8.13 [M + H]⁺ 498.0 (s,1H), 7.58 (s, 1H), 7.48 (d, J = 6.4 Hz, 1H), 7.08 (s, 1H), 5.46 (dd, J =6.4, 2.0 Hz, 1H), 3.77 (s, 3H), 3.55- 3.23 (m, 2H), 3.30 (d, J = 7.0 Hz,1H), 3.28-3.26 (m, 1H), 1.40 (t, J = 7.6 Hz, 3H). C61 ¹H NMR (600 MHz,CDCl₃) δ 8.16 [M + H]⁺ 432.0 (s, 1H), 7.67 (s, 1H), 7.08 (s, 1H),6.32-6.30 (m, 2H), 5.01-5.00 (m, 1H), 4.98-4.96 (m, 1H), 4.82-4.70 (m,2H), 4.08 (dd, J = 8.6, 2.4 Hz, 2H), 1.25 (t, J = 8.6 Hz, 3H). C62 ¹HNMR (600 MHz, CDCl₃) δ 8.16 [M + H]⁺ 464.1 (s, 1H), 7.67 (s, 1H), 7.08(s, 1H), 6.68 (s, 1H), 6.32-6.30 (m, 2H), 5.01-5.00 (m, 1H), 4.98-4.96(m, 1H), 4.82- 4.70 (m, 2H), 4.08 (dd, J = 8.6, 2.4 Hz, 2H), 2.36 (s,3H), 2.30 (s, 3H), 1.25 (t, J-8.6 Hz, 3H). C63 ¹H NMR (600 MHz, CDCl₃) δ8.16 [M + H]⁺ 548.0 (s, 1H), 7.67 (s, 1H), 7.08 (s, 1H), 6.32-6.30 (m,2H), 5.01-5.00 (m, 1H), 4.98-4.96 (m, 1H), 4.08 (dd, J = 8.7, 2.4 Hz,2H), 3.78 (s, 3H), 3.57 (s, 3H), 1.25 (t, J = 8.7 Hz, 3H).

Embodiment 4: Synthesis of Compounds a-1 to a-138 by Using a Method D

Method D:

Taking a compound a-44 for example, a specific preparation process wasas follows:

S1:5-amino-1H-pyrazole-3-cyano

Ethyl 2,3-dicyanopropionate (1.0 mmol) was added to 20.0 mL of ethanoland stirred vigorously, then hydrazine hydrate (2.0 mmol) was added tothe reaction solution, heated and refluxed, then the heating was stoppedafter 3 hours, and the mixture was cooled to room temperature. Themixture was concentrated in vacuum and extracted with ethyl acetate andwater, then the obtained ethyl acetate was concentrated and extracted invacuum to obtain white solid 5-amino-1H-pyrazole-3-cyano, and theintermediate was directly used for next step without furtherpurification.

S2:5,5-dichloro-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline[3,2-e]pyridine-2-cyano

Under the protection of nitrogen, a DMF mixture of5-amino-1H-pyrazole-3-cyano (1.0 mmol),2-bromo-3-(trichloromethyl)-5-trifluoromethylpyridine (1.0 mmol),cuprous iodide (0.2 mmol) and cesium carbonate (0.5 mmol) was stirred at120° C. for 24 hours. The mixture was cooled to room temperature, andthen filtered, and concentrated in vacuum, and the residues werepurified by column chromatography to obtain the target compound5,5-dichloro-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline[3,2-e]pyridine-2-cyano(yield of the two steps: 25%).

S3:5,5-dichloro-7-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline[3,2-e]pyridine-2-cyano

Under the protection of nitrogen, an anhydrous toluene mixture of5,5-dichloro-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline[3,2-e]pyridine-2-cyano(0.2 mmol), trifluoromethylsulfinyl chloride (0.5 mmol) anddimethylamine p-toluenesulfonate was stirred and heated at 100° C. for24 hours. The mixture was cooled to room temperature, and then filtered,and concentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound5,5-dichloro-7-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline[3,2-e]pyridine-2-cyano(yield: 77%).

The compounds a-1 to a-138 were synthesized with reference to the methodof the compound a-44 (wherein cyclization steps also included similarcyclization methods mentioned in documents such as Tetrahedron Letters(2015) 56: 1367; WO2016046404, and WO2013174822), with a difference thatdifferent raw materials were selected for reaction according todifferent target compounds, or the compounds were derived from thesynthesized target products through hydrolysis, simple esterification oramidation or reduction-oxidation. Specific compounds were as shown inTable 7.

TABLE 7 Compound Structure with a General Formula Shown in Formula (a)Structural formula Compound R¹ R² R³ R⁴ R⁵ R⁶ Formula a-1 —CN —SOCF₃ H—CO₂Me —CH₂CO₂Me 5-CF₃ (a) a-2 —CH₂CN a-3 —CH₂CONH₂ a-4 —CH₂CONHCH₃ a-5—CH₂CH₂OH a-6 —CH(CO₂Me)CH₃ a-7 —CH₃ —CH₂CO₂Me a-8 —CH₂CH₂Cl —CH₂CO₂Mea-9 H —CH₂CO₂Et a-10 —CH₂CO₂CH₂CF₃ a-11 —CH₂CO₂CH₂CHF₂ a-12—CH₂CO₂CH(CF₃)₂ a-13 —CH₂CO₂C(CH₃)₂CF₃ a-14 —CH₂CO₂C(CF₃)₂CH₃ a-15—CH₂CO₂CH(CF₃)OCH₃ a-16 —CH₂Ph a-17 —CH₂COCH₃ a-18 —CH₂Br a-19 —CH₂CF₃a-20 —CH₂COCF₃ a-21 —SOCH₂CH₃ —CH₂CO₂Me a-22 —SOCF₃ H —CO₂Et —CH₂CO₂Eta-23 —CH₂CO₂Me a-24 —CH₂CO₂CH₂CF₃ a-25 —COCF₃ —CH₂COCF₃ a-26 —CH₂COCH₃a-27 —CH₂Ph a-28 —CH₂CO₂Me a-29 —CH₂Br a-30 —CH₂CN a-31 —CH₂CF₃ a-32—COCH₃ —CH₂COCH₃ a-33 —CH₂CO₂Me a-34 —CH₂Br a-35 —CH₂CN a-36 —CH₂CF₃a-37 —CH₂COCF₃ a-38 —CONHMe —CH₂COCH₃ a-39 —CH₂CO₂Me a-40 —CH₂Br a-41—CH₂CF₃ a-42 —CH₂COCF₃ a-43 —NHMe —CH₂CN a-44 —Cl —Cl a-45 —CH₂Br a-46—CH₂Cl a-47 —CH₂CN a-48 —CH₂CF₃ a-49 —Br —CH₂Cl a-50 —CH₂COCF₃ a-51 —CH₃—CH₃ a-52 —CN —CN a-53 —CH₂CN a-54 —CH₂CF₃ a-55 —CH₂Cl a-56 —CH₂CO₂Mea-57 —CH₂COCF₃ a-58 CF₃ —CF₃ a-59 —CH₂CN a-60 —CH₂CF₃ a-61 —CH₂Cl a-62—CH₂CO₂Me a-63 —CH₂COCF₃ a-64 —CN —SOCF₃ H H —CO₂Me a-65 —CH₂CO₂Me a-66—CH(CO₂Me)CH₃ a-67 —CH₂CO₂CH₂CF₃ a-68 —CO₂CH₂CF₃ a-69 —CH₂CO₂CH(CF₃)₂a-70 —CH₂COCF₃ a-71 —COCF₃ a-72 —CN a-73 —CH₂CN a-74 —CF₃ a-75 —CH₂CF₃a-76 —CONHMe a-77 —CH₂CONHCH₃ a-78 —CH₂COCH₃ a-79 —COCH₃ a-80 —Cl a-81—Br a-82 —CH₂Cl a-83 —CH₂CH₂Cl a-84 —CHCHCl a-85 —CH(CH₃)₂ a-86—CH═CHCH₃ a-87 —CF₃ —SOCF₃ H H —CO₂Me a-88 —CH₂CO₂Me a-89 —CH(CO₂Me)CH₃a-90 —CH₂CO₂CH₂CF₃ a-91 —CO₂CH₂CF₃ a-92 —CH₂CO₂CH(CF₃)₂ a-93 —CH₂COCF₃a-94 —COCF₃ a-95 —CN a-96 —CH₂CN a-97 —CF₃ a-98 —CH₂CF₃ a-99 —CONHMea-100 —CH₂CONHCH₃ a-101 —CH₂COCH₃ a-102 —COCH₃ a-103 —Cl a-104 —Br a-105—CH₂Cl a-106 —CH₂CH₂Cl a-107 —CHCHCl a-108 —CH(CH₃)₂ a-109 —CH═CHCH₃a-110 —CN —CCF₃ H H —CO₂Me a-111 —CH₂CO₂Me a-112 —CH(CO₂Me)CH₃ a-113—CH₂CO₂CH₂CF₃ a-114 —CO₂CH₂CF₃ a-115 —CH₂CO₂CH(CF₃)₂ a-116 —CH₂COCF₃a-117 —COCF₃ a-118 —CN a-119 —CH₂CN a-120 —CF₃ a-121 —CH₂CF₃ a-122—CONHMe a-123 —CH₂CONHCH₃ a-124 —CH₂COCH₃ a-125 —COCH₃ a-126 —Cl a-127—Br a-128 —CH₂Cl a-129 —CH₂CH₂Cl a-130 —CHCHCl a-131 —CH(CH₃)₂ a-132—CH═CHCH₃ a-133 —CN —Cl H —CO₂Me —CH₂CO₂Me a-134 —CF₃ a-135 —OCF₃ a-136—CF₃ —CN a-137 —OCF₃ a-138 —SOCF₃

Embodiment 5: Synthesis of Compounds b-1 to b-138 by Using a Method E

Method E:

Taking a compound b-87 for example, a specific synthesis process was asfollows:

S1: 5-amino-1H-pyrazole-3-trifluoromethyl (Referring to Document Journalof Medical Chemistry (2017) 60: 5099)

Under the protection of nitrogen, sodium hydride (2.5 mmol) was added to20 ml of anhydrous tetrahydrofuran at 0° C., then anhydrous acetonitrile(2.0 mmol) and ethyl trifluoroacetate (1.0 mmol) were added to thereaction solution, heated and refluxed, and then the heating was stoppedafter 20 hours. The mixture was cooled to room temperature, andconcentrated in vacuum. The mixture was extracted with ethyl ether andwater, and diluted hydrochloric acid was added to adjust a pH to 2, thenthe mixture was extracted with ethyl ether, and concentrated in vacuumto obtain brown oily matter 4,4,4-trifluoro-3-carbonyl butyronitrile.The intermediate was directly used in next step without furtherpurification.

Methanesulfonic acid (2.0 ml) was added to a mixture of4,4,4-trifluoro-3-carbonyl butyronitrile (1.0 mmol) and hydrazinehydrate (1.0 ml), and the mixture was heated to 80° C. and reacted for10 hours. Then, water and ethyl acetate were added for extraction, andconcentrated in vacuum. The residues obtained were purified by columnchromatography to obtain the target compound5-amino-1H-pyrazole-3-trifluoromethyl which was as a yellow liquid(yield of the two steps: 15%), 1H NMR (400 MHz, DMSO-d6): δ 12.15 (s,1H), 5.53 (s, 1H), 5.35 (s, 2H).

S2:6-chloro-2-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline[4,3-e]pyridine-5-methylformate

Under the protection of nitrogen, a DMF mixture of5-amino-1H-pyrazole-3-trifluoromethyl (1.0 mmol),2-bromo-2-(3-bromo-5-chloropyridine-4-yl)-methyl acetate (1.0 mmol),cuprous iodide (0.2 mmol) and sodium ethoxide (0.5 mmol) was stirred at100° C. for 24 hours. The mixture was cooled to room temperature, andthen concentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound6-chloro-2-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline[4,3-e]pyridine-5-methylformate (yield: 35%).

S3:6-chloro-2-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline[4,3-e]pyridine-5-methylformate

Under the protection of nitrogen, an anhydrous toluene mixture of6-chloro-2-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline[4,3-e]pyridine-5-methylformate (0.2 mmol), trifluoromethylsulfinyl chloride (0.5 mmol) anddimethylamine p-toluenesulfonate was stirred and heated at 100° C. for24 hours. The mixture was cooled to room temperature, and thenconcentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound6-chloro-2-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline[4,3-e]pyridine-5-methylformate, wherein the yield was 85%.

The compounds b-1 to b-138 were synthesized with reference to the methodof the compound b-87 (wherein cyclization steps also included similarcyclization methods mentioned in documents such as SyntheticCommunications (2015) 45: 2426; Tetrahedron Letters (2014) 55: 4997; andWO2007149907) with a difference that different raw materials wereselected for reaction according to different target compounds, or thecompounds were derived from the synthesized target products throughhydrolysis, simple esterification or amidation or reduction-oxidation.Specific compounds were as shown in Table 8.

TABLE 8 Compound Structure with a General Formula Shown in Formula (b)Structural formula Compound R¹ R² R³ R⁴ R⁵ R⁶ Formula b-1 —CN  SOCF₃ H—CO₂Me —CH₂CO₂Me 5-Cl (b) b-2 —CH₂CN b-3 —CH₂CONH₂ b-4 —CH₂CONHCH₃ b-5—CH₂CH₂OH b-6 —CH(CO₂Me)CH₃ b-7 —CH₃ —CH₂CO₂Me b-8 —CH₂CH₂Cl —CH₂CO₂Meb-9 H —CH₂CO₂Et b-10 —CH₂CO₂CH₂CF₃ b-11 —CH₂CO₂CH₂CHF₂ b-12—CH₂CO₂CH(CF₃)₂ b-13 —CH₂CO₂C(CH₃)₂CF₃ b-14 —CH₂CO₂C(CF₃)₂CH₃ b-15—CH₂CO₂CH(CF₃)OCH₃ b-16 —CH₂Ph b-17 —CH₂COCH₃ b-18 —CH₂Br b-19 —CH₂CF₃b-20 —CH₂COCF₃ b-21 —SOCH₂CH₃ —CH₂CO₂Me b-22 —SOCF₃ H —CO₂Et —CH₂CO₂Etb-23 —CH₂CO₂Me b-24 —CH₂CO₂CH₂CF₃ b-25 —COCF₃ —CH₂COCF₃ b-26 —CH₂COCH₃b-27 —CH₂Ph b-28 —CH₂CO₂Me b-29 —CH₂Br b-30 —CH₂CN b-31 —CH₂CF₃ b-32—COCH₃ —CH₂COCH₃ b-33 —CH₂CO₂Me b-34 —CH₂Br b-35 —CH₂CN b-36 —CH₂CF₃b-37 —CH₂COCF₃ b-38 —CONHMe —CH₂COCH₃ b-39 —CH₂CO₂Me b-40 —CH₂Br b-41—CH₂CF₃ b-42 —CH₂COCF₃ b-43 —NHMe —CH₂CN b-44 —Cl —Cl b-45 —CH₂Br b-46—CH₂Cl b-47 —CH₂CN b-48 —CH₂CF₃ b-49 —Br —CH₂Cl b-50 —CH₂COCF₃ b-51 —CH₃—CH₃ b-52 —CN —CN b-53 —CH₂CN b-54 —CH₂CF₃ b-55 —CH₂Cl b-56 —CH₂CO₂Meb-57 —CH₂COCF₃ b-58 CF₃ —CF₃ b-59 —CH₂CN b-60 —CH₂CF₃ b-61 —CH₂Cl b-62—CH₂CO₂Me b-63 —CH₂COCF₃ b-64 —CN —SOCF₃ H H —CO₂Me b-65 —CH₂CO₂Me b-66—CH(CO₂Me)CH₃ b-67 —CH₂CO₂CH₂CF₃ b-68 —CO₂CH₂CF₃ b-69 —CH₂CO₂CH(CF₃)₂b-70 —CH₂COCF₃ b-71 —COCF₃ b-72 —CN b-73 —CH₂CN b-74 —CF₃ b-75 —CH₂CF₃b-76 —CONHMe b-77 —CH₂CONHCH₃ b-78 —CH₂COCH₃ b-79 —COCH₃ b-80 —Cl b-81—Br b-82 —CH₂Cl b-83 —CH₂CH₂Cl b-84 —CHCHCl b-85 —CH(CH₃)₂ b-86—CH═CHCH₃ b-87 —CF₃ —SOCF₃ H H —CO₂Me b-88 —CH₂CO₂Me b-89 —CH(CO₂Me)CH₃b-90 —CH₂CO₂CH₂CF₃ b-91 —CO₂CH₂CF₃ b-92 —CH₂CO₂CH(CF₃)₂ b-93 —CH₂COCF₃b-94 —COCF₃ b-95 —CN b-96 —CH₂CN b-97 —CF₃ b-98 —CH₂CF₃ b-99 —CONHMeb-100 —CH₂CONHCH₃ b-101 —CH₂COCH₃ b-102 —COCH₃ b-103 —Cl b-104 —Br b-105—CH₂Cl b-106 —CH₂CH₂Cl b-107 —CHCHCl b-108 —CH(CH₃)₂ b-109 —CH═CHCH₃b-110 —CN —OCF₃ H H —CO₂Me b-111 —CH₂CO₂Me b-112 —CH(CO₂Me)CH₃ b-113—CH₂CO₂CH₂CF₃ b-114 —CO₂CH₂CF₃ b-115 —CH₂CO₂CH(CF₃)₂ b-116 —CH₂COCF₃b-117 —COCF₃ b-118 —CN b-119 —CH₂CN b-120 —CF₃ b-121 —CH₂CF₃ b-122—CONHMe b-123 —CH₂CONHCH₃ b-124 —CH₂COCH₃ b-125 —COCH₃ b-126 —Cl b-127—Br b-128 —CH₂Cl b-129 —CH₂CH₂Cl b-130 —CHCHCl b-131 —CH(CH₃)₂ b-132—CH═CHCH₃ b-133 —CN —Cl H —CO₂Me —CH₂CO₂Me b-134 —CF₃ b-135 —OCF₃ b-136—CF3 —CN b-137 —OCF₃ b-138 —SOCF₃

Embodiment 6: Synthesis of Compounds c-1 Toc-349 by Using a Method F

Method F:

Taking a compound c-27 for example, a specific synthesis process was asfollows:

S1:6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-ethylformate

Under the protection of nitrogen, a DMF mixture of5-amino-1H-pyrazole-3-cyano (1.0 mmol),2-bromo-2-(2-bromo-6-chloro-4-trifluoromethylphenyl)diethyl malate (1.0mmol), cuprous iodide (0.2 mmol) and caesium carbonate (0.5 mmol) wasstirred at 100° C. for 24 hours. The mixture was cooled to roomtemperature, and then filtered. The filtrate was concentrated in vacuum,and the residues were purified by column chromatography to obtain thetarget compound6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-ethylformate (yield: 30%).

S2:6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-ethylformate

Under the protection of nitrogen, an anhydrous toluene mixture of6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-ethylformate (0.2 mmol), trifluoromethylsulfinyl chloride (0.5 mmol) anddimethylamine p-toluenesulfonate was stirred and heated at 100° C. for24 hours. The mixture was cooled to room temperature, and thenconcentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-ethylformate, wherein the yield was 82%.

S3:2-(6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-yl)-aceticacid

6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-ethylformate (1.0 mmol) was dissolved in 5 ml of dioxane, and then 10 ml of1N HCl was added thereto. The mixture was heated and refluxed for 5hours, and then ethyl acetate was added for extraction. Then the mixturewas concentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound2-(6-chloro-2-cyano-5-(2′2-diethoxy)-8-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[1,5-]quinazoline-5-yl)-aceticacid, wherein the yield was 78.

The compounds c-1 to c-349 were synthesized with reference to the methodof the compound c-27 (wherein cyclization steps also included similarcyclization methods mentioned in documents such as WO2007144669) with adifference that different raw materials were selected for reactionaccording to different target compounds, or the compounds were derivedfrom the synthesized target products through hydrolysis, simpleesterification or amidation or reduction-oxidation. Specific compoundswere as shown in Table 9.

TABLE 9 Compound Structure with a General Formula Shown in Formula (c)Structural formula Compound R¹ R² R³ R⁴ R⁵ R⁶ General c-1 —CN —CN H—CO₂Me —CH₂CO₂Me 3-Cl, and formula c-2 —CF₃ 5-CF₃ (c) c-3 —OCF₃ c 4 —CF₃—CN c-5 —CF₃ c-6 —OCF₃ c-7 —SOCF₃ c-8 —CN —SOCF₃ H —CO₂Me —CH₂CO₂Me c-9—CH₂CN c-10 —CH₂CONH₂ c-11 —CH₂CONHCH₃ c-12 —CH₂CH₂OH c-13 —CH(CO₂Me)CH₃c-14 —CH₃ —CO₂Me c-15 —Ac c-16 —CH₂CH₂Cl c-17 H —CH₂CO₂Et c-18 —COOHc-19 —CH₂CO₂CH₂CF₃ c-20 —CH₂CO₂CH₂CHF₂ c-21 —CH₂CO₂CH(CF₃)₂ c-22—CH₂CO₂C(CH₃)₂CF₃ c-23 —CH₂CO₂C(CF₃)₂CH₃ c-24 —CH₂CO₂C(CF₃)OCH₃ c-25—CO₂Et —CH₂CO₂Me c-26 —CH₂CO₂Et c-27 —CH₂CO₂H c-28 —CH₂CO₂CH₂CF₃ c-29—CH₂CO₂CH₂CHF₂ c-30 —CH₂CO₂CH(CF₃)₂ c-31 —CH₂CO₂C(CH₃)₂CF₃ c-32—CH₂CO₂C(CF₃)₂CH₃ c-33 —CH₂CO₂C(CF₃)OCH₃ c-34 —COCF₃ —CH₂COCF₃ c-35—CH₂COCH₃ c-36 —CH₂Ph c-37 —CH(CH₃)₂ c-38 —CH₂CO₂Me c-39 —COCH₃ c-40—CO₂Me c-41 —CH₂Br c-42 —CH₂CH₂Cl c-43 —CN c-44 —CH₂CN c-45 —CF₃ c-46—CH₂CF₃ c-47 —COCH₃ —CH₂COCF₃ c-48 —CH₂COCH₃ c-49 —CH₂Ph c-50 —CH(CH₃)₂c-51 —CH₂CO₂Me c-52 —COCH₃ c-53 —CO₂Me c-54 —CH₂Br c-55 —CH₂CH₂Cl c-56—CN c-57 —CH₂CN c-58 —CF₃ c-59 —CH₂CF₃ c-60 —CO₂Me —CO₂Me c-61 —CH₂Phc-62 —CH₃ c-63 —CH₂COCH₃ c-64 —CH₂Br c-65 —CH₂CH₂Cl c-66 —Br c-67 —CNc-68 —CF₃ c-69 —CH₂CF₃ c-70 —CH₂COCF₃ c-71 —CONHMe —CH₂COCH₃ c-72 —COCH₃c-73 —CO₂Me c-74 —CH₂CO₂Me c-75 —CH₂Ph c-76 —CH₃ c-77 —Br c-78 —CH₂Brc-79 —CH₂CH₂Cl c-80 —CN c-81 —CH₂CN c-82 —CF₃ c-83 —CH₂CF₃ c-84—CH₂COCF₃ c-85 —COCF₃ c-86 —F —F c-87 —Cl —Cl c-88 —CH₂Br c-89 —CH₂Clc-90 —CN c-91 —CH₂CN c-92 —CF₃ c-93 —CH₂CF₃ c-94 —Br —Br c-95 —CH₂Clc-96 —CH₂COCF₃ c-97 —COCF₃ c-98 —CH₃ —CH₃ c-99 —CH₂CH₃ c-100 —CN —CNc-101 —CH₂CN c-102 —CF₃ c-103 —CH₂CF₃ c-104 —CH₂Cl c-105 —CH₂CO₂Me c-106—COCH₃ c-107 —COCF₃ c-108 —CH₂COCF₃ c-109 —CF₃ —CF₃ c-110 —CH₂CF₃ c-111—CH₂CN c-112 —CH₂Cl c-113 —CH₂CO₂Me c-114 —COCH₃ c-115 —COCF₃ c-116—CH₂COCF₃ c-117 —CO₂nBu —CH₂CO₂nBu c-118 —SOCH₂CH₃ —CO₂Me —CH₂CO₂Mec-119 —CN —SOCF₃ H H —CO₂Me c-120 —CH₂CO₂Me c-121 —C(CO₂Me)CH₃ c-122—CH₂CO₂CH₂CF₃ c-123 —CO₂CH₂CF₃ c-124 —CH₂CO₂CH(CF₃)₂ c-125 —CH₂COCF₃c-126 —COCF₃ c-127 —CN c-128 —CH₂CN c-129 —CF₃ c-130 —CH₂CF₃ c-131—CONHMe c-132 —CH₂CONHCH₃ c-133 —CH₂COCH₃ c-134 —COCH₃ c-135 —Cl c-136—Br c-137 —CH₂Cl c-138 —CH₂CH₂Cl c-139 —CH═CHCl c-140 —CH(CH₃)₂ c-141—CH═CHCH₃ c-142 —CF₃ —SOCF₃ H H —CO₂Me c-143 —CH₂CO₂Me c-144—C(CO₂Me)CH₃ c-145 —CH₂CO₂CH₂CF₃ c-146 —CO₂CH₂CF₃ c-147 —CH₂CO₂CH(CF₃)₂c-148 —CH₂COCF₃ c-149 —COCF₃ c-150 —CN c-151 —CH₂CN c-152 —CF₃ c-153—CH₂CF₃ c-154 —CONHMe c-155 —CH₂CONHCH₃ c-156 —CH₂COCH₃ c-157 —COCH₃c-158 —Cl c-159 —Br c-160 —CH₂Cl c-161 —CH₂CH₂Cl c-162 —CH═CHCl c-163—CH(CH₃)₂ c-164 —CH═CHCH₃ c-165 —CN —OCF₃ H H —CO₂Me c-166 —CH₂CO₂Mec-167 —C(CO₂Me)CH₃ c-168 —CH₂CO₂CH₂CF₃ c-169 —CO₂CH₂CF₃ c-170—CH₂CO₂CH(CF₃)₂ c-171 —CH₂COCF₃ c-172 —COCF₃ c-173 —CN c-174 —CH₂CNc-175 —CF₃ c-176 —CH₂CF₃ c-177 —CONHMe c-178 —CH₂CONHCH₃ c-179 —CH₂COCH₃c-180 —COCH₃ c-181 —Cl c-182 —Br c-183 —CH₂Cl c-184 —CH₂CH₂Cl c-185—CH═CHCl c-186 —CH(CH₃)₂ c-187 —CH═CHCH₃ c-188 —CN —SOCF₃ H —CO₂Me—CH₂CO₂Me 3-Br, and c-189 —CH₂CO₂Et 5-CF₃ c-190 —CH₂CO₂CH₂CF₃ c-191—CH₂CO₂CH₂CHF₂ c-192 —CO₂Et —CH₂CO₂Me c-193 —CH₂CO₂Et c-194 —CO₂Me—CH₂CO₂Me 3-CF₃, and c-195 —CH₂CO₂Et 5-CF₃ c-196 —CH₂CO₂CH₂CF₃ c-197—CH₂CO₂CH₂CHF₂ c-198 —CO₂Et —CH₂CO₂Me c-199 —CH₂CO₂Et c-200 —CO₂Me—CH₂CO₂Me 3-Me, and c-201 —CH₂CO₂Et 5-CF₃ c-202 —CH₂CO₂CH₂CF₃ c-203—CH₂CO₂CH₂CHF₂ c-204 —CO₂Et —CH₂CO₂Me c-205 —CH₂CO₂Et c-206 —CO₂Me—CH₂CO₂Me 3-CN, c-207 —CH₂CO₂Et and 5- c-208 —CH₂CO₂CH₂CF₃ CF₃ c-209—CH₂CO₂CH₂CHF₂ c-210 —CO₂Et —CH₂CO₂Me c-211 —CH₂CO₂Et c-212 —CO₂Me—CH₂CO₂Me 3-CO₂Me, c-213 —CH₂CO₂Et and 5-CF₃ c-214 —CH₂CO₂CH₂CF₃ c-215—CH₂CO₂CH₂CHF₂ c-216 —CO₂Et —CH₂CO₂Me c-217 —CH₂CO₂Et c-218 —CO₂Me—CH₂CO₂Me 3-NO₂, c-219 —CH₂CO₂Et and c-220 —CH₂CO₂CH₂CF₃ 5-CF₃ c-221—CH₂CO₂CH₂CHF₂ c-222 —CO₂Et —CH₂CO₂Me c-223 —CH₂CO₂Et c-224 —CN —SOCF₃ H—CO₂Me —CH₂CO₂Me 3-Cl, c-225 —CH₂CO₂Et and 5- c-226 —CH₂CO₂CH₂CF₃ OCF₃c-227 —CH₂CO₂CH₂CHF₂ c-228 —CO₂Et —CH₂CO₂Me c-229 —CH₂CO₂Et c-230 —CO₂Me—CH₂CO₂Me 3-Br, c-231 —CH₂CO₂Et and 5- c-232 —CH₂CO₂CH₂CF₃ OCF₃ c-233—CH₂CO₂CH₂CHF₂ c-234 —CO₂Et —CH₂CO₂Me c-235 —CH₂CO₂Et c-236 —CO₂Me—CH₂CO₂Me 3-Me, c-237 —CH₂CO₂Et and 5- c-238 —CH₂CO₂CH₂CF₃ OCF₃ c-239—CH₂CO₂CH₂CHF₂ c-240 —CO₂Et —CH₂CO₂Me c-241 —CH₂CO₂Et c-242 —CO₂Me—CH₂CO₂Me 3-CN, c-243 —CH₂CO₂Et and 5- c-244 —CH₂CO₂CH₂CF₃ OCF₃ c-245—CH₂CO₂CH₂CHF₂ c-246 —CO₂Et —CH₂CO₂Me c-247 —CH₂CO₂Et c-248 —CO₂Me—CH₂CO₂Me 3-CH₃, c-249 —CH₂CO₂Et and c-250 —CH₂CO₂CH₂CF₃ 5-OCF₃ c-251—CH₂CO₂CH₂CHF₂ c-252 —CO₂Et —CH₂CO₂Me c-253 —CH₂CO₂Et c-254 —CO₂Me—CH₂CO₂Me 3-CO₂Me, c-255 —CH₂CO₂Et and c-256 —CH₂CO₂CH₂CF₃ 5-OCF₃ c-257—CH₂CO₂CH₂CHF₂ c-258 —CO₂Et —CH₂CO₂Me c-259 —CH₂CO₂Et c-260 —CO₂Me—CH₂CO₂Me 3-NO₂, c-261 —CH₂CO₂Et and c-262 —CH₂CO₂CH₂CF₃ 5-OCF₃ c-263—CH₂CO₂CH₂CHF₂ c-264 —CO₂Et —CH₂CO₂Me c-265 —CH₂CO₂Et c-266 —CN —SOCF₃ H—CO₂Me —CH₂CO₂Me 3-Cl, c-267 —CH₂CO₂Et and 5-NO₂ c-268 —CH₂CO₂CH₂CF₃c-269 —CH₂CO₂CH₂CHF₂ c-270 —CO₂Et —CH₂CO₂Me c-271 —CH₂CO₂Et c-272 —CO₂Me—CH₂CO₂Me 3-Br, c-273 —CH₂CO₂Et and 5- c-274 —CH₂CO₂CH₂CF₃ NO₂ c-275—CH₂CO₂CH₂CHF₂ c-276 —CO₂Et —CH₂CO₂Me c-277 —CH₂CO₂Et c-278 —CO₂Me—CH₂CO₂Me 3-Me, c-279 —CH₂CO₂Et and 5- c-280 —CH₂CO₂CH₂CF₃ NO₂ c-281—CH₂CO₂CH₂CHF₂ c-282 —CO₂Et —CH₂CO₂Me c-283 —CH₂CO₂Et c-284 —CO₂Me—CH₂CO₂Me 3-CN, c-285 —CH₂CO₂Et and 5- c-286 —CH₂CO₂CH₂CF₃ NO₂ c-287—CH₂CO₂CH₂CHF₂ c-288 —CO₂Et —CH₂CO₂Me c-289 —CH₂CO₂Et c-290 —CO₂Me—CH₂CO₂Me 3-CF₃, c-291 —CH₂CO₂Et and 5- c-292 —CH₂CO₂CH₂CF₃ NO₂ c-293—CH₂CO₂CH₂CHF₂ c-294 —CO₂Et —CH₂CO₂Me c-295 —CH₂CO₂Et c-296 —CO₂Me—CH₂CO₂Me 3-CO₂Me, c-297 —CH₂CO₂Et and 5-NO₂ c-298 —CH₂CO₂CH₂CF₃ c-299—CH₂CO₂CH₂CHF₂ c-300 —CO₂Et —CH₂CO₂Me c-301 —CH₂CO₂Et c-302 —CO₂Me—CH₂CO₂Me 3-NO₂, c-303 —CH₂CO₂Et and c-304 —CH₂CO₂CH₂CF₃ 5-NO₂ c-305—CH₂CO₂CH₂CHF₂ c-306 —CO₂Et —CH₂CO₂Me c-307 —CH₂CO₂Et c-308 —CN —SOCF₃ H—CO₂Me —CH₂CO₂Me 3-Cl, and c-309 —CH₂CO₂Et 5-Cl c-310 —CH₂CO₂CH₂CF₃c-311 —CH₂CO₂CH₂CHF₂ c-312 —CO₂Et —CH₂CO₂Me c-313 —CH₂CO₂Et c-314 —CO₂Me—CH₂CO₂Me 3-Br, and c-315 —CH₂CO₂Et 5-Cl c-316 —CH₂CO₂CH₂CF₃ c-317—CH₂CO₂CH₂CHF₂ c-318 —CO₂Et —CH₂CO₂Me c-319 —CH₂CO₂Et c-320 —CO₂Me—CH₂CO₂Me c-321 —CH₂CO₂Et 3-Me, c-322 —CH₂CO₂CH₂CF₃ and 5-Cl c-323—CH₂CO₂CH₂CHF₂ c-324 —CO₂Et —CH₂CO₂Me c-325 —CH₂CO₂Et c-326 —CO₂Me—CH₂CO₂Me 3-CN, c-327 —CH₂CO₂Et and 5- c-328 —CH₂CO₂CH₂CF₃ Cl c-329—CH₂CO₂CH₂CHF₂ c-330 —CO₂Et —CH₂CO₂Me c-331 —CH₂CO₂Et c-332 —CO₂Me—CH₂CO₂Me 3-CF₃, c-333 —CH₂CO₂Et and 5-Cl c-334 —CH₂CO₂CH₂CF₃ c-335—CH₂CO₂CH₂CHF₂ c-336 —CO₂Et —CH₂CO₂Me c-337 —CH₂CO₂Et c-338 —CO₂Me—CH₂CO₂Me 3-CO₂Me, c-339 —CH₂CO₂Et and 5-Cl c-340 —CH₂CO₂CH₂CF₃ c-341—CH₂CO₂CH₂CHF₂ c-342 —CO₂Et —CH₂CO₂Me c-343 —CH₂CO₂Et c-344 —CO₂Me—CH₂CO₂Me 3-NO₂, and c-345 —CH₂CO₂Et 5-Cl c-346 —CH₂CO₂CH₂CF₃ c-347—CH₂CO₂CH₂CHF₂ c-348 —CO₂Et —CH₂CO₂Me c-349 —CH₂CO₂Et

Embodiment 7: Synthesis of Compounds d-1 to d-142 by Using a Method G

Method G:

Taking a compound d-12 for example, a specific synthesis process was asfollows:

S1:9-chloro-2-cyano-3-cyclohexanethiol-5-(2′2-dimethoxy)-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-methylformate (Referring to Document Synthetic Communications (2012) 42: 3472)

Under the protection of nitrogen, an anhydrous acetonitrile mixture of9-chloro-2-cyano-5-(2′2-dimethoxy)-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-methylformate (2.0 mmol, synthesized with a method similar to S of thecompound c-27, with a yield of 26%), dicyclohexyl disulfide (1.0 mmol),ferric tribromide (0.5 mmol) and elemental iodine (0.5 mmol) was stirredat 85° C. for 24 hours. The mixture was cooled to room temperature, andthen concentrated in vacuum, and the residues were purified by columnchromatography to obtain the target compound9-chloro-2-cyano-3-cyclohexanethiol-5-(2′2-dimethoxy)-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-methylformate (yield: 90%).

S2:9-chloro-2-cyano-3-cyclohexanesulfinyl-5-(2′2-dimethoxy)-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-methylformate

9-chloro-2-cyano-3-cyclohexanethiol-5-(2′2-dimethoxy)-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-methylformate (1.0 mmol) was dissolved in anhydrous methylene chloride, andcooled to −15° C. Then, m-chloroperoxybenzoic acid (85%, 1.1 mmol) wasadded thereto, and the mixture was reacted at low temperature for 1 hourunder stirring. The mixture was cooled to room temperature, added withan aqueous solution of sodium hydrogen carbonate, extracted withmethylene chloride, and concentrated in vacuum. The residues werepurified by column chromatography to obtain the target compound9-chloro-2-cyano-3-cyclohexanesulfinyl-5-(2′2-dimethoxy)-7-trifluoromethyl-4,5-dihydropyrazole[1,5-α]quinazoline-5-methylformate, wherein the yield was 97%.

The compounds d-1 to d-142 were synthesized with reference to the methodof the compound d-12 (wherein cyclization steps also included similarcyclization methods mentioned in documents such as Tetrahedron Letters(2015) 56: 1367; WO2016046404; Synthetic Communications (2015) 45: 2426;Tetrahedron Letters (2014) 55: 4997; and WO2007149907), with adifference that different raw materials were selected for reactionaccording to different target compounds, or the compounds were derivedfrom the synthesized target products through hydrolysis, simpleesterification or amidation or reduction-oxidation. Specific compoundswere as shown in Table 10.

TABLE 10 CompoundStructure with a General FormulaShown in Formula (d)Structural formula Compound R¹ R² R³ R⁴ R⁵ R⁶ General d-1 —CN —CF₃ H—CO₂Me —CH₂CO₂Me 4-CF₃, formula d-2 —Br and 6-Cl (d) d-3 —OCF₃ d-4 —Cld-5 —CF₃ —CF₃ d-6 —OCF₃ d-7 —CN d-8 —COCH₃ —SOCF₃ H —CO₂Me —CH₂CO₂Me d-9—CH₂NH₂ d-10 —CN —SOPh d-11 —SOCH₂Ph d-12 —SOC₆H₁₃ d-13 —SOCH₃ d-14—SOCH₂CH₃ d-15

d-16

d-17

d-18

d-19 —CF₃ —SOCF₃ H —CO₂Me —CH₂CO₂Me d-20 —CN —SOCF₃ H —CO₂Me —CH₂CONH₂d-21 —CH₂CONHCH₃ d-22 —CH₂CON(CH₃)₂ d-23 —CH₂CH₂OH d-24 —CH(CO₂Me)CH₃d-25 —CH₂CO₂H d-26 —CH₂CO₂Et d-27 —CH₂CO₂CH₂CF₃ d-28 —CH₂CO₂CH₂CHF₂ d-29—CH₂CO₂CH(CF₃)₂ d-30 —CH₂CO₂C(CH₃)₂CF₃ d-31 —CH₂CO₂C(CF₃)₂CH₃ d-32—CH₂CO₂CH(CF₃)OCH₃ d-33 —CH₂COCH₃ d-34 —CH₂Br d-35 —CH₂CF₃ d-36—CH₂COCF₃ d-37 —CO₂Et —CH₂CO₂Et d-38 —CH₂CO₂H d-39 —CH₂CO₂Me d-40—CH₂CO₂CH₂CF₃ d-41 —CH₂CO₂CH₂CHF₂ d-42 —CH₂CO₂CH(CF₃)₂ d-43—CH₂CO₂C(CH₃)₂CF₃ d-44 —CH₂CO₂C(CF₃)₂CH₃ d-45 —CH₂CO₂CH(CF₃)OCH₃ d-46—COCH₃ —CH₂COCH₃ d-47 —CH₂CO₂Me d-48 —CH₂CF₃ d-49 —CH₂COCF₃ d-50 —COCF₃—CH₂COCF₃ d-51 —CH₂COCH₃ d-52 —CH₂Ph d-53 —CH(CH₃)₂ d-54 —CH₂CO₂Me d-55—CH₂CF₃ d-56 —CONHMe —CH₂COCF₃ d-57 —CH₂Br d-58 —NHMe —CH₂CN d-59 —Cld-60 —Cl —CH₂CN d-61 —CH₂CF₃ d-62 —Br —CH₂Cl d-63 —CH₂COCF₃ d-64—CH₂COCF₃ d-65 —CN —CH₂CF₃ d-66 —CH₂Cl d-67 —CH₂CO₂Me d-68 —CF₃—CH₂COCF₃ d-69 —CH₂CF₃ d-70 —CH₂CN d-71 —CH₂CO₂Me d-72 —CO₂nBu—CH₂CO₂nBu d-73 —COOCH(CH₃)₂ —COOCH(CH₃)₂ d-74 —CN —SOCF₃ H H —CO₂Med-75 —CH₂CO₂Me d-76 —C(CO₂Me)CH₃ d-77 —CH₂CO₂CH₂CF₃ d-78 —CO₂CH₂CF₃ d-79—CH₂CO₂CH(CF₃)2 d-80 —CH₂COCF₃ d-81 —COCF₃ d-82 —CN d-83 —CH₂CN d-84—CF₃ d-85 —CH₂CF₃ d-86 —CONHMe d-87 —CH₂CONHCH₃ d-88 —CH₂COCH₃ d-89—COCH₃ d-90 —Cl d-91 —Br d-92 —CH₂Cl d-93 —CH₂CH₂Cl d-94 —CH═CHCl d-95—CH(CH₃)₂ d-96 —CH═CHCH₃ d-97 —CF₃ —SOCF₃ H H —CO₂Me d-98 —CH₂CO₂Me d-99—C(CO₂Me)CH₃ d-100 —CH₂CO₂CH₂CF₃ d-101 —CO₂CH₂CF₃ d-102 —CH₂CO₂CH(CF₃)2d-103 —CH₂COCF₃ d-104 —COCF₃ d-105 —CN d-106 —CH₂CN d-107 —CF₃ d-108—CH₂CF₃ d-109 —CONHMe d-110 —CH₂CONHCH₃ d-111 —CH₂COCH₃ d-112 —COCH₃d-113 —Cl d-114 —Br d-115 —CH₂Cl d-116 —CH₂CH₂Cl d-117 —CH═CHCl d-118—CH(CH₃)₂ d-119 —CH═CHCH₃ d-120 —CN —OCF₃ H H —CO₂Me d-121 —CH₂CO₂Med-122 —C(CO₂Me)CH₃ d-123 —CH₂CO₂CH₂CF₃ d-124 —CO₂CH₂CF₃ d-125—CH₂CO₂CH(CF₃)2 d-126 —CH₂COCF₃ d-127 —COCF₃ d-128 —CN d-129 —CH₂CNd-130 —CF₃ d-131 —CH₂CF₃ d-132 —CONHMe d-133 —CH₂CONHCH₃ d-134 —CH₂COCH₃d-135- —COCH₃ d-136 —Cl d-137 —Br d-138 —CH₂Cl d-139 —CH₂CH₂Cl d-140—CH═CHCl d-141 —CH(CH₃)₂ d-142 —CH═CHCH₃

Embodiment 8: Synthesis of Compounds e-1 to e-24 by Using a Method H

Method H:

The compounds e-1 to e-24 were synthesized with the methods of thecompound series c and (wherein cyclization steps also included similarcyclization methods mentioned in documents such as WO2016046404;WO2013174822; Synthetic Communications (2015) 45: 2426; TetrahedronLetters (2014) 55: 4997; and WO2007149907), with a difference thatdifferent raw materials were selected for reaction according todifferent target compounds, or the compounds were derived from thesynthesized target products through hydrolysis, simple esterification oramidation or reduction-oxidation. Specific compounds were as shown inTable 11.

TABLE 11 Compound Structure with a General Formula Shown in Formula (e)Structural formula Compound R¹ R² R³ R⁴ R⁵ R⁶ General e-1 —CN —SOCF₃ H—CO₂Me —CH₂CO₂Me 3-Cl, and 6-CF₃ formula e-2 —CH₂CO₂Et (e) e-3—CH₂CO₂CH₂CF₃ e-4 —CH₂CO₂CH₂CHF₂ e-5 —CO₂Et —CH₂CO₂Et e-6 —CH₂CO₂Me e-7—CN —SOCF₃ H —CO₂Me —CH₂CO₂Me 3-Cl, and 4-CF₃ e-8 —CH₂CO₂Et e-9—CH₂CO₂CH₂CF₃ e-10 —CH₂CO₂CH₂CHF₂ e-11 —CO₂Et —CH₂CO₂Et e-12 —CH₂CO₂Mee-13 —CN —SOCF₃ H —CO₂Me —CH₂CO₂Me 5-Cl, and 6-CF₃ e-14 —CH₂CO₂Et e-15—CH₂CO₂CH₂CF₃ e-16 —CH₂CO₂CH₂CHF₂ e-17 —CO₂Et —CH₂CO₂Et e-18 —CH₂CO₂Mee-19 —CN —SOCF₃ H —CO₂Me —CH₂CO₂Me 4-Cl, and 5-CF₃ e-20 —CH₂CO₂Et e-21—CH₂CO₂CH₂CF₃ e-22 —CH₂CO₂CH₂CHF₂ e-23 —CO₂Et —CH₂CO₂Et e-24 —CH₂CO₂Me

Hydrogen spectrum and mass spectrum data of nuclear magnetic resonanceof some compounds shown in the general formula (a) of Table 7 were shownin Table 12.

TABLE 12 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance of Some Compounds Shown in General Formula (a) Com- pound¹H-NMR(600 MHz) MS (ESI) a-1 ¹H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺512.1 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 3.74 (s, 3H), 3.60(s, 3H),3.33-3.25(m, 2H). a-2 ¹H NMR (600 MHz, CDCl₃) δ 8.43 [M + H]⁺ 479.0 (s,1H), 7.60 (s, 1H), 7.20 (brs, 1H), 3.61(s, 3H), 3.31-3.26(m, 2H). a-3 ¹HNMR (600 MHz, CDCl₃) δ 8.36 [M + H]⁺ 497.1 (s, 1H), 7.50 (s, 1H), 7.49(brs, 1H), 6.98 (brs, 2H), 3.74(s, 3H), 3.33-3.25(m, 2H). a-4 ¹H NMR(600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 510.9 (s, 1H), 7.55 (s, 1H), 7.49 (brs,1H), 7.24 (brs, 1H), 3.74(s, 3H), 3.33-3.25(m, 2H), 2.80(s, 3H). a-5 ¹HNMR (600 MHz, CDCl₃) δ 8.37 [M + H]⁺ 484.2 (s, 1H), 7.45 (s, 1H), 7.39(brs, 1H), 4.34 (brs, 1H), 3.80(dd, J = 6.4, 2.0 Hz, 2H), 3.74(s, 3H),3.34-3.25(dd, J = 6.4, 2.0 Hz, 2H). a-6 ¹H NMR (600 MHz, CDCl₃) δ 8.37[M + H]⁺ 526.0 (s, 1H), 7.45 (s, 1H), 7.39 (brs, 1H), 3.84 (s, 3H),3.74(s, 3H), 3.25(dd, J = 5.4, 1.80 Hz, 1H), 1.14(d, J = 8.0, 3H). a-7¹H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 526.1 (s, 1H), 7.56 (s, 1H),3.74 (s, 3H), 3.60(s, 3H), 3.33-3.25(m, 2H), 3.04 (s, 3H). a-8 ¹H NMR(600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 574.1 (s, 1H), 7.56 (s, 1H), 3.74 (s,3H), 3.60(s, 3H), 3.63-3.55(m, 2H), 3.53-3.48(m, 2H), 3.33-3.25(m, 2H).a-9 ¹H NMR (600 MHz, CDCl₃) δ 8.37 [M + H]⁺ 526.0 (s, 1H), 7.45 (s, 1H),7.39 (brs, 1H), 3.84 (dd, J = 5.4, 1.80 Hz, 2H), 3.74(s, 3H),3.34-3.25(m, 2H), 1.14(t, J = 8.0, 3H). a-10 ¹H NMR (600 MHz, CDCl₃) δ8.36 [M + H]⁺ 580.0 (s, 1H), 8.15 (s, 1H), 7.54 (t, J = 2.3 Hz, 1H),4.78-4.63 (m, 2H), 4.49-4.29 (m, 2H), 3.82 (d, J = 4.8 Hz, 3H),3.71-3.46 (m, 2H). a-11 ¹H NMR (600 MHz, CDCl₃) δ 8.34 [M + H]⁺ 562.1(s, 1H), 7.59 (s, 1H), 6.92 (s, 1H), 5.87 (tdt, J = 54.7, 24.2, 3.9 Hz,1H), 4.35-4.12 (m, 2H), 3.83 (d, J = 6.8 Hz, 3H), 3.63-3.35 (m, 2H).a-12 ¹H NMR (600 MHz, CDCl₃) δ 8.16 [M + H]⁺ 648.2 (s, 1H), 7.61 (s,1H), 6.95 (s, 1H), 5.69- 5.59 (m, 1H), 3.85 (d, J = 21.5 Hz, 3H),3.81-3.62 (m, 2H). a-14 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 662.2(d, J = 1.8 Hz, 1H), 7.60 (d, J = 1.3 Hz, 1H), 6.87 (s, 1H), 3.83 (s,3H), 3.71-3.50 (m, 2H), 1.87 (s, 1H). a-16 ¹H NMR (600 MHz, CDCl₃) δ8.35 [M + H]⁺ 530.1 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 7.23-7.19(m,5H), 3.74 (s, 3H), 3.33-3.25(m, 2H). a-17 ¹H NMR (600 MHz, CDCl₃) δ 8.35[M + H]⁺ 496.0 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 3.74 (s, 3H),3.33-3.25(m, 2H), 2.10 (s, 3H). a-18 ¹H NMR (600 MHz, CDCl₃) δ 8.35 [M +H]⁺ 531.9 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 3.72 (s, 3H),3.13-3.05(m, 2H). a-19 H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 521.9 (s,1H), 7.56 (s, 1H), 7.45 (brs, 1H), 3.68 (s, 3H), 3.03-2.95(m, 2H). a-20¹H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 549.9 (s, 1H), 7.56 (s, 1H),7.45 (brs, 1H), 3.72 (s, 3H), 3.10-3.04(m, 2H). a-21 ¹H NMR (600 MHz,CDCl₃) δ 8.07 [M + H]⁺ 472.0 (S, 1H), 7.57 (S, 1H), 7.40 (s, 1H), 3.80(d, J = 16.4 Hz, 3H), 3.61 (d, J = 31.8 Hz, 3H), 3.51-3.40 (m, 1H),3.46- 3.29 (m, 1H), 3.20-2.98 (m, 2H), 1.38-1.29 (m, 3H). a-22 ¹H NMR(600 MHz, CDCl₃) δ 8.10 [M + H]⁺ 540.0 (m, 1H), 7.57 (s, 1H), 7.27 (s,1H), 4.38- 4.21 (m, 2H), 4.15-4.00 (m, 2H), 3.69-3.30 (m, 2H), 1.25 (td,J = 7.1, 1.4 Hz, 3H), 1.17 (dt, J = 16.7, 7.1 Hz, 3H). a-26 ¹H NMR (600MHz, CDCl₃) δ 8.35 [M + H]⁺ 534.0 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H),3.33-3.25(m, 2H), 2.10 (s, 3H). a-27 ¹H NMR (600 MHz, CDCl₃) δ 8.35 [M +H]⁺ 568.1 (s, 1H), 7.55 (s, 1H), 7.44 (brs, 1H), 7.23-7.19(m, 5H),3.33-3.25(m, 2H). a-28 ¹H NMR (600 MHz, CDCl₃) δ 8.38 [M + H]⁺ 550.1 (s,1H), 7.53 (s, 1H), 7.45 (brs, 1H), 3.74 (s, 3H), 3.33-3.25(m, 2H). a-29¹H NMR (600 MHz, CDCl₃) δ 8.36 [M + H]⁺ 569.9 (s, 1H), 7.49 (s, 1H),7.46 (brs, 1H), 3.13-3.06(m, 2H). a-30 ¹H NMR (600 MHz, CDCl₃) δ 8.39[M + H]⁺ 516.9 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 3.13-3.05(m, 2H).a-36 ¹H NMR (600 MHz, CDCl₃) δ 8.39 [M + H]⁺ 506.0 (s, 1H), 7.53 (s,1H), 7.40 (brs, 1H), 3.13-3.05(m, 2H), 2.40 (s, 3H). a-37 ¹H NMR (600MHz, CDCl₃) δ 8.37 [M + H]⁺ 534.0 (s, 1H), 7.46 (s, 1H), 7.39 (brs, 1H),3.11-3.06(m, 2H), 2.38 (s, 3H). a-44 ¹H NMR (600 MHz, CDCl₃) δ 8.35 [M +H]⁺ 449.9 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H). a-45 ¹H NMR (600 MHz,CDCl₃) δ 8.35 [M + H]⁺ 507.8 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H),3.13-3.05(m, 2H). a-47 ¹H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 544.8 (s,1H), 7.55 (s, 1H), 7.45 (brs, 1H), 3.10-3.02(m, 2H). a-51 ¹H NMR (600MHz, CDCl₃) δ 8.35 [M + H]⁺ 409.9 (s, 1H), 7.56 (s, 1H), 7.45 (brs,1H),1.37 (s, 6H). a-52 ¹H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 432.0 (s,1H), 7.56 (s, 1H), 7.45 (brs, 1H). a-53 ¹H NMR (600 MHz, CDCl₃) δ 8.33[M + H]⁺ 544.8 (s, 1H), 7.50 (s, 1H), 7.40 (brs, 1H), 3.10-3.02(m, 2H).a-56 ¹H NMR (600 MHz, CDCl₃) δ [M + H]⁺ 479.1 8.35 (s, 1H), 7.56 (s,1H), 7.45 (brs, 1H), 3.60(s, 3H), 3.33-3.25(m, 2H). a-57 ¹H NMR (600MHz, CDCl₃) δ 8.36 [M + H]⁺ 517.1 (s, 1H), 7.58 (s, 1H), 7.47 (brs, 1H),3.13-3.05(m, 2H). a-59 ¹H NMR (600 MHz, CDCl₃) δ 8.23 [M + H]⁺ 488.8 (s,1H), 7.47 (s, 1H), 7.20 (brs, 1H), 3.00-2.92(m, 2H). a-62 ¹H NMR (600MHz, CDCl₃) δ 8.35 [M + H]⁺ 522.1 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H),3.60(s, 3H), 3.31-3.23(m, 2H). a-63 ¹H NMR (600 MHz, CDCl₃) δ 8.33 [M +H]⁺ 559.9 (s, 1H), 7.55 (s, 1H), 7.40 (brs, 1H), 3.14-3.05(m, 2H). a-64¹H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 440.1 (s, 1H), 7.56 (s, 1H),7.45 (brs, 1H), 4.74 (s, 1H), 3.60(s, 3H). a-65 ¹H NMR (600 MHz, CDCl₃)δ 8.35 [M + H]⁺ 454.1 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 4.74 (s,1H), 3.60(s, 3H), 3.33-3.25(m, 2H). a-71 ¹H NMR (600 MHz, CDCl₃) δ 8.35[M + H]⁺ 477.9 (s, 1H), 7.58 (s, 1H), 7.43 (brs, 1H), 4.75 (s, 1H). a-72¹H NMR (600 MHz, CDCl₃) δ 8.30 [M + H]⁺ 407.0 (s, 1H), 7.50 (s, 1H),7.41 (brs, 1H), 4.65 (s, 1H). a-80 ¹H NMR (600 MHz, CDCl₃) δ 8.38 [M +H]⁺ 415.9 (s, 1H), 7.61 (s, 1H), 7.38 (brs, 1H), 4.81 (s, 1H). a-83 ¹HNMR (600 MHz, CDCl₃) δ 8.38 [M + H]⁺ 444.1 (s, 1H), 7.61 (s, 1H), 7.38(brs, 1H), 4.81 (s, 1H), 3.63-3.55(m, 2H), 3.53-3.48(m, 2H). a-86 ¹H NMR(600 MHz, CDCl₃) δ 8.39 [M + H]⁺ 441.9 (s, 1H), 7.58 (s, 1H), 7.48 (brs,1H), 6.23(d, J = 8.3 Hz, 1H), 6.02(dd, J = 1.3, 8.3 Hz, 1H), 4.81 (s,1H). a-87 ¹H NMR (600 MHz, CDCl₃) δ 8.25 [M + H]⁺ 483.1 (s, 1H), 7.55(s, 1H), 7.35 (brs, 1H), 4.74 (s, 1H), 3.60(s, 3H). a-88 ¹H NMR (600MHz, CDCl₃) δ 8.35 [M + H]⁺ 497.1 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H),4.74 (s, 1H), 3.60(s, 3H), 3.33-3.25(m, 2H). a-95 ¹H NMR (600 MHz,CDCl₃) δ 8.30 [M + H]⁺ 449.9 (s, 1H), 7.50 (s, 1H), 7.41 (brs, 1H), 4.65(s, 1H). a-109 ¹H NMR (600 MHz, CDCl₃) δ 8.39 [M + H]⁺ 464.9 (s, 1H),7.58 (s, 1H), 7.48 (brs, 1H), 6.23(d, J = 8.3 Hz, 1H), 6.02(dd, J = 1.3,8.3 Hz, 1H), 4.81 (s, 1H), 1.63(d, J = 9.3 Hz, 3H). a-111 ¹H NMR (600MHz, CDCl₃) δ 8.36 [M + H]⁺ 422.1 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H),4.74 (s, 1H), 3.60(s, 3H), 3.32-3.25(m, 2H). a-118 ¹H NMR (600 MHz,CDCl₃) δ 8.30 [M + H]⁺ 375.1 (s, 1H), 7.50 (s, 1H), 7.41 (brs, 1H), 4.65(s, 1H). a-122 ¹H NMR (600 MHz, CDCl₃) δ 8.35 [M + H]⁺ 407.1 (s, 1H),7.65 (s, 1H), 7.50 (brs, 1H), 7.42 (brs, 1H), 4.65 (s, 1H), 2.82 (s,3H). a-132 ¹H NMR (600 MHz, CDCl₃) δ 8.40 [M + H]⁺ 389.9 (s, 1H), 7.58(s, 1H), 7.48 (brs, 1H), 6.23(d, J = 8.3 Hz, 1H), 6.02(dd, J = 1.3, 8.3Hz, 1H), 4.81 (s, 1H), 1.63(d, J = 9.3 Hz, 3H). a-133 ¹H NMR (600 MHz,CDCl₃) δ 8.45 [M + H]⁺ 430.1 (s, 1H), 7.51 (s, 1H), 7.43 (brs, 1H), 3.76(s, 3H), 3.61(s, 3H), 3.31-3.25(m, 2H). a-134 ¹H NMR (600 MHz, CDCl₃) δ8.35 [M + H]⁺ 464.1 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 3.71 (s, 3H),3.64(s, 3H), 3.32-3.26(m, 2H). a-136 ¹H NMR (600 MHz, CDCl₃) δ 8.30 [M +H]⁺ 464.1 (s, 1H), 7.55 (s, 1H), 7.47 (brs, 1H), 3.74 (s, 3H), 3.66(s,3H), 3.35-3.29(m, 2H).

Hydrogen spectrum and mass spectrum data of nuclear magnetic resonanceof some compounds shown in the general formula (b) of Table 8 were shownin Table 13.

TABLE 13 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance of Some Compounds Shown in General Formula (b) Com- pound¹H-NMR(600 MHz) MS (ESI) b-1 ¹H NMR (600 MHz, CDCl₃) δ 8.85 [M + H]⁺478.0 (s, 1H), 7.96 (s, 1H), 7.45 (brs, 1H), 3.74 (s, 3H), 3.60(s, 3H),3.32-3.25(m, 2H). b-2 ¹H NMR (600 MHz, CDCl₃) δ 8.86 [M + H]⁺ 445.0 (s,1H), 7.97 (s, 1H), 7.21 (brs, 1H), 3.62(s, 3H), 3.31-3.27(m, 2H). b-3 ¹HNMR (600 MHz, CDCl₃) δ 8.86 [M + H]⁺ 463.1 (s, 1H), 7.95 (s, 1H), 7.49(brs, 1H), 6.28 (brs, 2H), 3.73(s, 3H), 3.33-3.26(m, 2H). b-4 ¹H NMR(600 MHz, CDCl₃) δ 8.85 [M + H]⁺ 476.9 (s, 1H), 7.95 (s, 1H), 7.50 (brs,1H), 7.25 (brs, 1H), 3.73(s, 3H), 3.35-3.26(m, 2H), 2.81(s, 3H). b-5 ¹HNMR (600 MHz, CDCl₃) δ 8.87 [M + H]⁺ 450.1 (s, 1H), 7.85 (s, 1H), 7.49(brs, 1H), 4.44 (brs, 1H), 3.81(dd, J = 6.4, 2.0 Hz, 2H), 3.77(s, 3H),3.34-3.27(dd, J = 6.3, 2.1 Hz, 2H). b-6 ¹H NMR (600 MHz, CDCl₃) δ 8.87[M + H]⁺ 492.0 (s, 1H), 7.95 (s, 1H), 7.37 (brs, 1H), 3.85 (s, 3H),3.75(s, 3H), 3.25(dd, J = 5.5, 1.8 Hz, 1H), 1.15(d, J = 8.1, 3H). b-7 ¹HNMR (600 MHz, CDCl₃) δ 8.85 [M + H]⁺ 492.0 (s, 1H), 7.96 (s, 1H), 3.76(s, 3H), 3.61(s, 3H), 3.35-3.28(m, 2H), 3.06 (s, 3H). b-8 ¹H NMR (600MHz, CDCl₃) δ 8.86 [M + H]⁺ 540.0 (s, 1H), 7.98 (s, 1H), 3.75 (s, 3H),3.59(s, 3H), 3.69-3.59(m, 2H), 3.54-3.48(m, 2H), 3.35-3.2(m, 2H). b-9 ¹HNMR (600 MHz, CDCl₃) δ 8.89 [M + H]⁺ 492.0 (s, 1H), 7.47 (s, 1H), 7.34(brs, 1H), 3.83 (dd, J = 5.4, 1.8 Hz, 2H), 3.76(s, 3H), 3.35-3.26(m,2H), 1.13(t, J = 8.0, 3H). b-10 ¹H NMR (600 MHz, CDCl₃) δ 8.86 [M + H]⁺545.9 (s, 1H), 8.15 (s, 1H), 7.54 (t, J = 2.5 Hz, 1H), 4.79-4.63 (m,2H), 4.49-4.26 (m, 2H), 3.82 (d, J = 4.6 Hz, 3H), 3.72-3.46 (m, 2H).b-11 ¹H NMR (600 MHz, CDCl₃) δ 8.84 [M + H]⁺ 528.0 (s, 1H), 7.99 (s,1H), 6.95 (s, 1H), 5.89 (tdt, J = 54.7, 24.2, 3.9 Hz, 1H), 4.36-4.13 (m,2H), 3.83 (d, J = 6.9 Hz, 3H), 3.64-3.35 (m, 2H). b-12 ¹H NMR (600 MHz,CDCl₃) δ 8.96 [M + H]⁺ 613.9 (s, 1H), 7.67 (s, 1H), 6.96 (s, 1H),5.68-5.57 (m, 1H), 3.85 (d, J = 22.5 Hz, 3H), 3.81-3.62 (m, 2H). b-14 ¹HNMR (600 MHz, CDCl₃) δ 8.95 [M + H]⁺ 628.0 (d, J = 1.8 Hz, 1H), 7.90 (d,J = 1.3 Hz, 1H), 6.97 (s, 1H), 3.85 (s, 3H), 3.72-3.54 (m, 2H), 1.86 (s,1H). b-16 ¹H NMR (600 MHz, CDCl₃) δ 8.85 [M + H]⁺ 496.1 (s, 1H), 7.86(s, 1H), 7.49 (brs, 1H), 7.22-7.18(m, 5H), 3.75 (s, 3H), 3.32-3.25(m,2H). b-17 ¹H NMR (600 MHz, CDCl₃) δ 8.95 [M + H]⁺ 462.0 (s, 1H), 7.58(s, 1H), 7.46 (brs, 1H), 3.75 (s, 3H), 3.31-3.23(m, 2H), 2.13 (s, 3H).b-18 ¹H NMR (600 MHz, CDCl₃) δ 8.95 [M + H]⁺ 497.9 (s, 1H), 7.86 (s,1H), 7.44 (brs, 1H), 3.72 (s, 3H), 3.13-3.05(m, 2H). b-19 H NMR (600MHz, CDCl₃) δ 8.86 [M + H]⁺ 487.9 (s, 1H), 7.77 (s, 1H), 7.51 (brs, 1H),3.68 (s, 3H), 3.06-2.98(m, 2H). b-20 ¹H NMR (600 MHz, CDCl₃) δ 8.95 [M +H]⁺ 515.9 (s, 1H), 7.86 (s, 1H), 7.45 (brs, 1H), 3.73 (s, 3H),3.17-3.11(m, 2H). b-21 ¹H NMR (600 MHz, CDCl₃) δ 8.97 [M + H]⁺ 438.0 (S,1H), 7.97 (S, 1H), 7.48 (s, 1H), 3.81 (d, J = 16.5 Hz, 3H), 3.62 (d, J =31.2 Hz, 3H), 3.50-3.40 (m, 1H), 3.45-3.29 (m, 1H), 3.31-3.08 (m, 2H),1.39-1.30 (m, 3H). b-23 ¹H NMR (600 MHz, CDCl₃) δ 8.93 [M + H]⁺ 491.1(s, 1H), 7.97 (d, J = 1.9 Hz, 1H), 6.86 (brs, 1H), 4.40-4.20 (m, 2H),3.63 (s, 3H), 3.53-3.31 (m, 2H), 1.25 (td, J = 7.2, 3.0 Hz, 3H). b-25 ¹HNMR (600 MHz, CDCl₃) δ 8.93 [M + H]⁺ 553.9 (s, 1H), 7.97 (d, J = 1.9 Hz,1H), 6.86 (brs, 1H), 4.30-4.10 (m, 2H). b-27 ¹H NMR (600 MHz, CDCl₃) δ8.99 [M + H]⁺ 534.0 (s, 1H), 7.95 (s, 1H), 7.44 (brs, 1H), 7.23-7.19(m,5H), 3.35-3.25(m, 2H). b-28 ¹H NMR (600 MHz, CDCl₃) δ 8.98 [M + H]⁺515.9 (s, 1H), 7.93 (s, 1H), 7.45 (brs, 1H), 3.75 (s, 3H), 3.33-3.25(m,2H). b-30 ¹H NMR (600 MHz, CDCl₃) δ 8.99 [M + H]⁺ 482.9 (s, 1H), 7.86(s, 1H), 7.46 (brs, 1H), 3.13-3.05(m, 2H). b-34 ¹H NMR (600 MHz, CDCl₃)δ 8.99 [M + H]⁺ 481.9 (s, 1H), 7.83 (s, 1H), 7.41 (brs, 1H),3.14-3.06(m, 2H), 2.44 (s, 3H). b-37 ¹H NMR (600 MHz, CDCl₃) δ 8.97 [M +H]⁺ 499.9 (s, 1H), 7.86 (s, 1H), 7.39 (brs, 1H), 3.11-3.06(m, 2H), 2.9(s, 3H). b-43 ¹H NMR (600 MHz, CDCl₃) δ 8.85 [M + H]⁺ 416.0 (s, 1H),7.76 (s, 1H), 7.45 (brs, 1H), 5.45 (brs, 1H), 3.37 (s, 3H), 3.01-2.96(m,2H). b-47 ¹H NMR (600 MHz, CDCl₃) δ 8.95 [M + H]⁺ 420.9 (s, 1H), 7.85(s, 1H), 7.40 (brs, 1H), 3.18-3.09(m, 2H). b-48 ¹H NMR (600 MHz, CDCl₃)δ 8.95 [M + H]⁺ 463.9 (s, 1H), 7.85 (s, 1H), 7.40 (brs, 1H),3.01-2.89(m, 2H). b-50 ¹H NMR (600 MHz, CDCl₃) δ 8.89 [M + H]⁺ 535.8 (s,1H), 7.75 (s, 1H), 7.32 (brs, 1H), 2.91-2.79(m, 2H). b-54 ¹H NMR (600MHz, CDCl₃) δ 8.85 [M + H]⁺ 454.9 (s, 1H), 7.70 (s, 1H), 7.30 (brs, 1H),2.81-2.68(m, 2H). b-56 ¹H NMR (600 MHz, CDCl₃) δ 8.95 [M + H]⁺ 445.0 (s,1H), 7.86 (s, 1H), 7.45 (brs, 1H), 3.61(s, 3H), 3.35-3.25(m, 2H). b-57¹H NMR (600 MHz, CDCl₃) δ 8.96 [M + H]⁺ 482.9 (s, 1H), 7.78 (s, 1H),7.49 (brs, 1H), 3.14-3.05(m, 2H). b-59 ¹H NMR (600 MHz, CDCl₃) δ 8.93[M + H]⁺ 454.9 (s, 1H), 7.77 (s, 1H), 7.21 (brs, 1H), 3.01-2.95(m, 2H).b-62 ¹H NMR (600 MHz, CDCl₃) δ 8.95 [M + H]⁺ 487.9 (s, 1H), 7.76 (s,1H), 7.47 (brs, 1H), 3.61(s, 3H), 3.31-3.23(m, 2H). b-63 ¹H NMR (600MHz, CDCl₃) δ 8.93 [M + H]⁺ 525.9 (s, 1H), 7.75 (s, 1H), 7.42 (brs, 1H),3.15-3.07(m, 2H). b-66 ¹H NMR (600 MHz, CDCl₃) δ 8.87 [M + H]⁺ 434.0 (s,1H), 7.95 (s, 1H), 7.37 (brs, 1H), 4.74 (s, 1H), 3.75(s, 3H), 3.25(dd, J= 5.5, 1.9 Hz, 1H), 1.15(d, J = 8.1, 3H). b-68 ¹H NMR (600 MHz, CDCl₃) δ8.80 [M + H]⁺ 487.9 (s, 1H), 7.90 (s, 1H), 7.41 (brs, 1H), 4.65 (m, 1H),4.47 (s, 2H), 2.95-2.77(m, 2H). b-70 ¹H NMR (600 MHz, CDCl₃) δ 8.81 [M +H]⁺ 457.9 (s, 1H), 7.91 (s, 1H), 7.42 (brs, 1H), 4.65 (m, 1H),2.95-2.77(m, 2H). b-73 ¹H NMR (600 MHz, CDCl₃) δ 8.82 [M + H]⁺ 386.9 (s,1H), 7.92 (s, 1H), 7.41 (brs, 1H), 4.65 (m, 1H), 2.93-2.73(m, 2H). b-80¹H NMR (600 MHz, CDCl₃) δ 8.89 [M + H]⁺ 381.9 (s, 1H), 7.95 (s, 1H),7.42 (brs, 1H), 4.66 (m, 1H). b-86 ¹H NMR (600 MHz, CDCl₃) δ 8.89 [M +H]⁺ 388.0 (s, 1H), 7.98 (s, 1H), 7.49 (brs, 1H), 6.24(d, J = 8.4 Hz,1H), 6.03(dd, J = 1.4, 8.4 Hz, 1H), 4.82 (s, 1H). b-87 ¹H NMR (600 MHz,CDCl₃) δ 8.85 [M + H]⁺ 448.9 (s, 1H), 7.95 (s, 1H), 7.41 (brs, 1H), 4.75(s, 1H), 3.60(s, 3H). b-88 ¹H NMR (600 MHz, CDCl₃) δ 8.85 [M + H]⁺ 462.9(s, 1H), 7.96 (s, 1H), 7.45 (brs, 1H), 4.76 (s, 1H), 3.61(s, 3H),3.34-3.26(m, 2H). b-94 ¹H NMR (600 MHz, CDCl₃) δ 8.80 [M + H]⁺ 486.9 (s,1H), 7.80 (s, 1H), 7.47 (brs, 1H), 4.66 (s, 1H). b-99 ¹H NMR (600 MHz,CDCl₃) δ 8.81 [M + H]⁺ 447.9 (s, 1H), 7.82 (s, 1H), 7.27 (brs, 1H), 5.27(brs, 1H), 4.66 (s, 1H), 2.86 (s, 3H). b-104 ¹H NMR (600 MHz, CDCl₃) δ8.80 [M + H]⁺ 468.8 (s, 1H), 7.78 (s, 1H), 7.38 (brs, 1H), 4.89 (s, 1H).b-111 ¹H NMR (600 MHz, CDCl₃) δ 8.86 [M + H]⁺ 388.0 (s, 1H), 7.86 (s,1H), 7.41 (brs, 1H), 4.68 (s, 1H), 3.61(s, 3H), 3.33-3.28(m, 2H). b-116¹H NMR (600 MHz, CDCl₃) δ 8.83 [M + H]⁺ 426.0 (s, 1H), 8.01 (s, 1H),7.39 (brs, 1H), 4.66 (m, 1H), 2.96-2.77(m, 2H). b-118 ¹H NMR (600 MHz,CDCl₃) δ 8.90 [M + H]⁺ 341.0 (s, 1H), 7.80 (s, 1H), 7.37 (brs, 1H), 4.65(s, 1H). b-123 ¹H NMR (600 MHz, CDCl₃) δ 8.95 [M + H]⁺ 387.0 (s, 1H),7.95 (s, 1H), 7.42 (brs, 1H), 7.36 (brs, 1H), 4.75 (s, 1H), 3.11-3.06(m,2H), 2.82 (s, 3H). b-131 ¹H NMR (600 MHz, CDCl₃) δ 8.87 [M + H]⁺ 358.0(s, 1H), 7.91 (s, 1H), 7.42 (brs, 1H), 4.75 (d, J = 8.1, 1H),2.11-2.06(m, 1H), 0.92 (d, J = 10.1, 6H). b-134 ¹H NMR (600 MHz, CDCl₃)δ 8.85 [M + H]⁺ 430.1 (s, 1H), 7.96 (s, 1H), 7.45 (brs, 1H), 3.71 (s,3H), 3.64(s, 3H), 3.32-3.26(m, 2H). b-135 ¹H NMR (600 MHz, CDCl₃) δ 8.89[M + H]⁺ 446.0 (s, 1H), 7.96 (s, 1H), 7.43 (brs, 1H), 3.73 (s, 3H),3.63(s, 3H), 3.31-3.27(m, 2H). b-136 ¹H NMR (600 MHz, CDCl₃) δ 8.90 [M +H]⁺ 430.0 (s, 1H), 7.95 (s, 1H), 7.47 (brs, 1H), 3.74 (s, 3H), 3.66(s,3H), 3.35-3.29(m, 2H). b-138 ¹H NMR (600 MHz, CDCl₃) δ 8.87(s, 1H), [M +H]⁺ 521.1 7.96 (s, 1H), 7.43 (brs, 1H), 3.72 (s, 3H), 3.66(s, 3H),3.32-3.26(m, 2H).

Hydrogen spectrum and mass spectrum data of nuclear magnetic resonanceof some compounds shown in the general formula (c) of Table 9 were shownin Table 14.

TABLE 14 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance of Some Compounds Shown in General Formula (c) Com- pound¹H-NMR(600 MHz) MS (ESI) c-2 ¹H NMR (600 MHz, CDCl₃) δ 8.14 (s, 1H),[M + H]⁺ 497.1 7.57 (s, 1H), 7.05 (brs, 1H), 3.82 (s, 3H), 3.64 (s, 3H),3.57-3.25 (m, 2H). c-4 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 497.2 (s,1H), 7.60 (s, 1H), 7.05 (brs, 1H), 3.82 (s, 3H), 3.64 (s, 3H), 3.57-3.25(m, 2H). c-7 ¹H NMR (600 MHz, CDCl₃) δ 8.20 (s, 1H), [M + H]⁺ 587.9 7.60(s, 1H), 7.05 (brs, 1H), 3.82 (s, 3H), 3.64 (s, 3H), 3.57-3.25 (m, 2H).c-8 ¹H NMR (600 MHz, CDCl₃) δ 8.13 (s, 1H), [M + H]⁺ 544.9 7.58 (s, 1H),7.28 (s, 1H), 3.82 (s, 3H), 3.66 (s, 3H), 3.55-3.23 (m, 2H). ¹H NMR (600MHz, CDCl₃) δ 8.14 (s, 1H), 7.57 (s, 1H), 6.82 (s, 1H), 3.82 (s, 3H),3.62 (s, 3H), 3.49 (d, J = 1.5 Hz, 2H). c-14 ¹H NMR (600 MHz, CDCl₃) δ8.15 [M + H]⁺ 559.1 (s, 1H), 7.56 (s, 1H), 3.84 (s, 3H), 3.60(s, 3H),3.33-3.25(m, 2H), 3.04 (s, 3H). c-15 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M +H]⁺ 587.1 (s, 1H), 7.56 (s, 1H), 3.84 (s, 3H), 3.60(s, 3H), 3.33-3.25(m,2H), 2.12 (s, 3H). c-17 ¹H NMR (600 MHz, CDCl₃) δ 8.13 (d, [M + H]⁺559.0 J = 1.3 Hz, 1H), 7.57 (d, J = 1.2 Hz, 1H), 6.84 (s, 1H), 4.11-3.99(m, 2H), 3.81 (s, 3H), 3.48 (d, J = 2.2 Hz, 2H), 1.16 (t, J = 7.1 Hz,3H). c-18 ¹H NMR (600 MHz, CDCl₃) δ 8.12 (d, [M + H]⁺ 530.9 J = 1.8 Hz,1H), 7.57 (d, J = 1.8 Hz, 1H), 7.03 (s, 1H), 3.81 (s, 3H), 3.59-3.33 (m,2H), 2.27 (s, 1H). c-19 ¹H NMR (600 MHz, CDCl₃) δ 8.18-8.13 [M + H]⁺612.9 (m, 1H), 7.66-7.56 (m, 1H), 6.87 (s, 1H), 4.48-4.31 (m, 2H), 3.83(d, J = 6.7 Hz, 3H), 3.70-3.48 (m, 2H). c-20 ¹H NMR (600 MHz, CDCl₃) δ8.14 (dd, [M + H]⁺ 595.0 J = 4.8, 1.7 Hz, 1H), 7.59 (d, J = 0.3 Hz, 1H),5.87 (tdt, J = 54.7, 23.8, 3.9 Hz, 1H), 4.33-4.14 (m, 2H), 3.83 (d, J =7.3 Hz, 3H), 3.60-3.37 (m, 2H). c-21 ¹H NMR (600 MHz, CDCl₃) δ 8.16 (s,1H), [M + H]⁺ 680.9 7.61 (s, 1H), 6.95 (s, 1H), 5.69- 5.59 (m, 1H), 3.85(d, J = 21.5 Hz, 3H), 3.81-3.62 (m, 2H). c-25 ¹H NMR (600 MHz, CDCl₃) δ8.13 (dd, [M + H]⁺ 559.0 J = 4.9, 1.8 Hz, 1H), 7.57 (d, J = 1.8 Hz, 1H),6.86 (s, 1H), 4.40-4.20 (m, 2H), 3.63 (d, J = 23.3 Hz, 3H), 3.53- 3.31(m, 2H), 1.25 (td, J = 7.1, 3.0 Hz, 3H). c-26 ¹H NMR (600 MHz, CDCl₃) δ8.15-8.10 [M + H]⁺ 572.9 (m, 1H), 7.57 (s, 1H), 7.27 (s, 1H), 4.38-4.21(m, 2H), 4.15-4.00 (m, 2H), 3.69-3.30 (m, 2H), 1.25 (td, J = 7.1, 1.4Hz, 3H), 1.17 (dt, J = 16.7, 7.1 Hz, 3H). c-28 ¹H NMR (600 MHz, CDCl₃) δ8.15 (dd, [M + H]⁺ 627.0 J = 4.5, 1.8 Hz, 1H), 7.65-7.57 (m, 1H), 6.84(s, 1H), 4.48-4.22 (m, 4H), 3.71-3.46 (m, 2H), 1.25 (td, J = 7.1, 1.1Hz, 3H). c-29 ¹H NMR (600 MHz, CDCl₃) δ 8.14 (dd, [M + H]⁺ 609.0 J =4.1, 1.8 Hz, 1H), 7.59 (t, J = 2.4 Hz, 1H), 5.88 (tdt, J = 54.7, 26.4,3.9 Hz, 1H), 4.43-4.16 (m, 4H), 3.60- 3.35 (m, 2H), 1.25 (t, J = 7.1 Hz,3H). c-34 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 620.9 (s, 1H), 7.56(s, 1H), 7.45 (brs, 1H), 3.33-3.25(m, 2H). c-36 ¹H NMR (600 MHz, CDCl₃)δ 8.15 [M + H]⁺ 601.0 (s, 1H), 7.55 (s, 1H), 7.44 (brs, 1H),7.23-7.19(m, 5H), 3.33-3.25(m, 2H). c-39 ¹H NMR (600 MHz, CDCl₃) δ 8.15[M + H]⁺ 552.9 (s, 1H), 7.55 (s, 1H), 7.44 (brs, 1H), 2.43(s, 3H). c-42¹H NMR (600 MHz, CDCl₃) δ 8.18 [M + H]⁺ 572.9 (s, 1H), 7.61 (s, 1H),7.38 (brs, 1H), 3.63-3.55(m, 2H), 3.53-3.48(m, 2H). c-47 ¹H NMR (600MHz, CDCl₃) δ 8.18 [M + H]⁺ 566.9 (s, 1H), 7.61 (s, 1H), 7.38 (brs, 1H),3.53-3.48(m, 2H), 2.49 (s, 3H). c-53 ¹H NMR (600 MHz, CDCl₃) δ 8.20 [M +H]⁺ 514.9 (s, 1H), 7.61 (s, 1H), 7.38 (brs, 1H), 3.59 (s, 3H), 2.49 (s,3H). c-54 ¹H NMR (600 MHz, CDCl₃) δ 8.18 [M + H]⁺ 549.0 (s, 1H), 7.61(s, 1H), 7.38 (brs, 1H), 3.23-3.19(m, 2H), 2.49 (s, 3H). c-57 ¹H NMR(600 MHz, CDCl₃) δ 8.18 [M + H]⁺ 495.9 (s, 1H), 7.61 (s, 1H), 7.38 (brs,1H), 3.13-3.08(m, 2H), 2.49 (s, 3H). c-61 ¹H NMR (600 MHz, CDCl₃) δ 8.13[M + H]⁺ 563.1 (d, J = 1.3 Hz, 1H), 7.57 (d, J = 1.2 Hz, 1H), 7.35-7.19(m, 5H), 6.84 (s, 1H), 3.81 (s, 3H), 3.53-3.38(m, 2H). c-64 ¹H NMR (600MHz, CDCl₃) δ 8.15 [M + H]⁺ 564.9 (d, J = 1.5 Hz, 1H), 7.57 (d, J = 1.2Hz, 1H), 6.84 (s, 1H), 3.81 (s, 3H), 3.33-3.20(m, 2H). c-67 ¹H NMR (600MHz, CDCl₃) δ 8.16 (d, [M + H]⁺ 497.9 J = 1.8 Hz, 1H), 7.57 (d, J = 1.2Hz, 1H), 6.84 (s, 1H). c-72 ¹H NMR (600 MHz, CDCl₃) δ 8.06 (d, [M + H]⁺512.9 J = 2.0 Hz, 1H), 7.67 (d, J = 1.2 Hz, 1H), 7.54 (s, 1H), 6.84 (s,1H), 2.94 (s, 3H), 2.46 (s, 3H). c-73 ¹H NMR (600 MHz, CDCl₃) δ 8.06 (d,[M + H]⁺ 530.0 J = 2.0 Hz, 1H), 7.67 (d, J = 1.2 Hz, 1H), 7.54 (s, 1H),6.84 (s, 1H), 3.74 (s, 3H), 2.86 (s, 3H). c-77 ¹H NMR (600 MHz, CDCl₃) δ8.06 (d, [M + H]⁺ 550.0 J = 2.0 Hz, 1H), 7.67 (d, J = 1.2 Hz, 1H), 7.54(s, 1H), 6.84 (s, 1H), 2.86 (s, 3H). c-80 ¹H NMR (600 MHz, CDCl₃) δ 8.07(d, [M + H]⁺ 496.9 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 7.54 (s,1H), 6.84 (s, 1H), 2.87 (s, 3H). c-84 ¹H NMR (600 MHz, CDCl₃) δ 8.06 (d,[M + H]⁺ 581.9 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 7.54 (s, 1H),6.84 (s, 1H), 3.13-3.08(m, 2H), 2.87 (s, 3H). c-86 ¹H NMR (600 MHz,CDCl₃) δ 8.07 (d, [M + H]⁺ 451.0 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz,1H), 6.84 (s, 1H). c-91 ¹H NMR (600 MHz, CDCl₃) δ 8.06 (d, [M + H]⁺487.9 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 6.88 (s, 1H),3.10-3.05(m, 2H). c-93 ¹H NMR (600 MHz, CDCl₃) δ 8.06 (d, [M + H]⁺ 530.9J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 6.88 (s, 1H), 2.50-2.35(m,2H). c-97 ¹H NMR (600 MHz, CDCl₃) δ 8.09 (d, [M + H]⁺ 588.8 J = 2.0 Hz,1H), 7.68 (d, J = 1.2 Hz, 1H), 6.88 (s, 1H). c-98 ¹H NMR (600 MHz,CDCl₃) δ 8.19 (d, [M + H]⁺ 443.1 J = 2.0 Hz, 1H), 7.70 (d, J = 1.2 Hz,1H), 6.88 (s, 1H), 1.38 (s, 6H). c-101 ¹H NMR (600 MHz, CDCl₃) δ 8.06(d, [M + H]⁺ 478.8 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 6.89 (s,1H), 3.11-3.05(m, 2H). c-105 ¹H NMR (600 MHz, CDCl₃) δ 8.06 (d, [M + H]⁺512.1 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 6.89 (s, 1H), 3.87 (s,3H), 3.11-3.05(m, 2H). c-107 ¹H NMR (600 MHz, CDCl₃) δ 8.11 (d, [M + H]⁺535.9 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 6.58 (s, 1H). c-110 ¹HNMR (600 MHz, CDCl₃) δ 8.07 (d, [M + H]⁺ 565.1 J = 2.0 Hz, 1H), 7.68 (d,J = 1.2 Hz, 1H), 6.89 (s, 1H), 2.91-2.75(m, 2H). c-111 ¹H NMR (600 MHz,CDCl₃) δ 8.08 (d, [M + H]⁺ 520.9 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz,1H), 6.95 (s, 1H), 3.11-2.95(m, 2H). c-114 ¹H NMR (600 MHz, CDCl₃) δ8.10 (d, [M + H]⁺ 524.9 J = 2.0 Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 6.95(s, 1H), 2.45(s, 3H). c-117 ¹H NMR (600 MHz, CDCl₃) δ 8.15 (s, 1H), [M +H]⁺ 629.0 7.59(s, 1H), 6.88 (s, 0H), 4.24- 4.19 (m, 2H), 4.08-3.93 (m,2H), 3.57-3.45 (m, 1H), 3.48-3.32 (m, 1H), 1.62-1.53 (m, 2H), 1.50(dddd, J = 13.7, 6.9, 3.5, 2.3 Hz, 2H), 1.31-1.19 (m, 4H), 1.01-0.81 (m,6H). c-118 ¹H NMR (600 MHz, CDCl₃) δ 8.18 (s, 1H), [M + H]⁺ 505.0 7.57(s, 1H), 7.45 (s, 1H), 3.80 (d, J = 16.4 Hz, 3H), 3.61 (d, J = 31.8 Hz,3H), 3.51-3.40 (m, 1H), 3.46- 3.29 (m, 1H), 3.20-2.98 (m, 2H), 1.38-1.29(m, 3H). c-123 ¹H NMR (600 MHz, CDCl₃) δ 8.10 (d, [M + H]⁺ 540.9 J = 2.0Hz, 1H), 7.68 (d, J = 1.2 Hz, 1H), 6.95 (s, 1H), 4.89 (s, 1H), 4.45(dd,J = 4.8, 1.7 Hz, 2H). c-126 ¹H NMR (600 MHz, CDCl₃) δ 8.11 (d, [M + H]⁺510.9 J = 2.0 Hz, 1H), 7.69 (d, J = 1.2 Hz, 1H), 6.95 (s, 1H), 4.89 (s,1H). c-128 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 453.9 (s, 1H), 7.69(s, 1H), 6.95 (brs, 1H), 3.74 (d, J = 6.9 Hz, 1H), 2.33-2.25(m, 2H).c-135 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 448.9 (s, 1H), 7.61 (s,1H), 6.39 (brs, 1H), 4.71 (s, 1H). c-139 ¹H NMR (600 MHz, CDCl₃) δ8.16(s, [M + H]⁺ 474.9 1H), 7.61 (s, 1H), 6.79 (brs, 1H), 6.59 (dd, J =12.8, 8.9 Hz, 1H), 6.09 (d, J = 8.9 Hz, 1H), 4.71 (d, J = 6.9 Hz, 1H).c-149 ¹H NMR (600 MHz, CDCl₃) δ 8.15 (d, [M + H]⁺ 553.9 J = 2.0 Hz, 1H),7.69 (d, J = 1.2 Hz, 1H), 6.95 (s, 1H), 4.90 (s, 1H). c-150 ¹H NMR (600MHz, CDCl₃) δ 8.20 (d, [M + H]⁺ 483.0 J = 2.0 Hz, 1H), 7.69 (d, J = 1.2Hz, 1H), 6.35 (s, 1H), 4.91 (s, 1H). c-152 ¹H NMR (600 MHz, CDCl₃) δ8.10 (d, [M + H]⁺ 525.9 J = 2.0 Hz, 1H), 7.65 (d, J = 1.2 Hz, 1H), 6.25(s, 1H), 4.71 (s, 1H). c-154 ¹H NMR (600 MHz, CDCl₃) δ 8.10 (d, [M + H]⁺514.9 J = 2.0 Hz, 1H), 7.65 (d, J = 1.2 Hz, 1H), 6.75 (brs, 1H), 6.25(brs, 1H), 4.70 (s, 1H), 2.93 (s, 3H). c-166 ¹H NMR (600 MHz, CDCl₃) δ8.16 (d, [M + H]⁺ 455.0 J = 2.0 Hz, 1H), 7.68 (d, J = 1.4 Hz, 1H), 6.89(s, 1H), 3.87 (s, 3H), 3.11-3.05(m, 2H). c-169 ¹H NMR (600 MHz, CDCl₃) δ8.06 (d, [M + H]⁺ 523.0 J = 2.0 Hz, 1H), 7.68 (d, J = 1.4 Hz, 1H), 6.89(s, 1H), 4.87 (d, J = 12.0 Hz, 1H), 4.67-4.60 (m, 2H), 3.11-3.05(m, 2H).c-173 ¹H NMR (600 MHz, CDCl₃) δ 8.05 (d, [M + H]⁺ 408.0 J = 2.0 Hz, 1H),7.69 (d, J = 1.2 Hz, 1H), 6.95 (s, 1H), 4.91 (s, 1H). c-180 ¹H NMR (600MHz, CDCl₃) δ 8.09 (d, [M + H]⁺ 439.0 J = 2.0 Hz, 1H), 7.68 (d, J = 1.4Hz, 1H), 6.89 (s, 1H), 4.87 (d, J = 12.0 Hz, 1H), 3.11-3.05(m, 2H),2.05(s, 2H). c-188 ¹H NMR (600 MHz, CDCl₃) δ 8.03 (s, 1H), [M + H]⁺589.0 7.88 (s, 1H), 7.28 (s, 1H), 3.82 (s, 3H), 3.66 (s, 3H), 3.55-3.23(m, 2H). c-196 ¹H NMR (600 MHz, CDCl₃) δ 8.08-8.13 [M + H]⁺ 647.0 (m,1H), 7.86-7.84 (m, 1H), 6.87 (s, 1H), 4.48-4.31 (m, 2H), 3.83 (d, J =6.7 Hz, 3H), 3.70-3.48 (m, 2H). c-203 ¹H NMR (600 MHz, CDCl₃) δ 8.04[M + H]⁺ 575.0 (s, 1H), 7.89 (s, 1H), 5.87 (tdt, J = 54.7, 23.8, 3.9 Hz,1H), 4.33-4.14 (m, 2H), 3.85 (d, J = 7.3 Hz, 3H), 3.60-3.37 (m, 2H).c-210 ¹H NMR (600 MHz, CDCl₃) δ 8.03 (dd, [M + H]⁺ 550.0 J = 4.9, 1.8Hz, 1H), 7.87 (d, J = 1.8 Hz, 1H), 6.86 (s, 1H), 4.40-4.20 (m, 2H), 3.63(d, J = 23.3 Hz, 3H), 3.53- 3.31 (m, 2H), 1.25 (td, J = 7.1, 3.0 Hz,3H). c-217 ¹H NMR (600 MHz, CDCl₃) δ 8.05 (m, 1H), [M + H]⁺ 597.0 7.87(s, 1H), 7.27 (s, 1H), 4.38- 4.21 (m, 2H), 4.15-4.00 (m, 2H), 3.69-3.30(m, 2H), 1.25 (td, J = 7.1, 1.4 Hz, 3H), 1.17 (dt, J = 16.7, 7.1 Hz,3H). c-221 ¹H NMR (600 MHz, CDCl₃) δ 8.04 (dd, [M + H]⁺ 606.0 J = 4.8,1.7 Hz, 1H), 7.59 (d, J = 0.3 Hz, 1H), 5.87 (tdt, J = 54.7, 23.8, 3.9Hz, 1H), 4.33-4.14 (m, 2H), 3.83 (d, J = 7.3 Hz, 3H), 3.60-3.37 (m, 2H).c-224 ¹H NMR (600 MHz, CDCl₃) δ 7.33 (s, 1H), [M + H]⁺ 560.9 6.86 (s,1H), 5.28 (s, 1H), 3.82 (s, 3H), 3.66 (s, 3H), 3.55-3.23 (m, 2H). c-231¹H NMR (600 MHz, CDCl₃) δ 7.43 (d, [M + H]⁺ 618.9 J = 1.3 Hz, 1H), 6.92(d, J = 1.2 Hz, 1H), 6.84 (s, 1H), 4.11-3.99 (m, 2H), 3.81 (s, 3H), 3.48(d, J = 2.2 Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H). c-238 ¹H NMR (600 MHz,CDCl₃) δ 6.88 (m, 1H), [M + H]⁺ 609.0 6.76 (m, 1H), 6.57 (s, 1H), 4.48-4.31 (m, 2H), 3.83 (d, J = 6.7 Hz, 3H), 3.70-3.48 (m, 2H). c-245 ¹H NMR(600 MHz, CDCl₃) δ 7.75 (dd, [M + H]⁺ 602.0 J = 4.8, 1.7 Hz, 1H), 7.28(d, J = 0.3 Hz, 1H), 5.87 (tdt, J = 54.7, 23.8, 3.9 Hz, 1H), 4.33-4.14(m, 2H), 3.83 (d, J = 7.3 Hz, 3H), 3.60-3.37 (m, 2H). c-253 ¹H NMR (600MHz, CDCl₃) δ 6.88 (m, 1H), [M + H]⁺ 569.0 6.74 (s, 1H), 5.27 (s, 1H),4.38- 4.21 (m, 2H), 4.15-4.00 (m, 2H), 3.69-3.30 (m, 2H), 1.25 (td, J =7.1, 1.4 Hz, 3H), 1.17 (dt, J = 16.7, 7.1 Hz, 3H). c-258 ¹H NMR (600MHz, CDCl₃) δ 7.53 [M + H]⁺ 599.0 (s, 1H), 7.37 (s, 1H), 6.86 (s, 1H),4.40- 4.20 (m, 2H), 4.34 (dd, J = 23.3,7.8 Hz, 2H), 3.63 (s, 3H), 3.55(s, 3H), 3.53- 3.31 (m, 2H), 1.25 (td, J = 7.1, 3.0 Hz, 3H). c-262 ¹HNMR (600 MHz, CDCl₃) δ 7.77 (m, 1H), [M + H]⁺ 640.0 7.36 (m, 1H), 6.87(s, 1H), 4.48- 4.31 (m, 2H), 3.83 (d, J = 6.7 Hz, 3H), 3.70-3.48 (m,2H). c-266 ¹H NMR (600 MHz, CDCl₃) δ 8.23 (s, 1H), [M + H]⁺ 522.0 7.88(s, 1H), 7.58 (s, 1H), 3.82 (s, 3H), 3.66 (s, 3H), 3.55-3.23 (m, 2H).c-273 ¹H NMR (600 MHz, CDCl₃) δ 8.43 (s, 1H), [M + H]⁺ 579.9 7.87 (s,1H), 7.54 (s, 1H), 4.11- 3.99 (m, 2H), 3.81 (s, 3H), 3.48 (d, J = 2.2Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H). c-286 ¹H NMR (600 MHz, CDCl₃) δ 8.55(m, 1H), [M + H]⁺ 581.0 8.26 (m, 1H), 6.87 (s, 1H), 4.48- 4.31 (m, 2H),3.83 (d, J = 6.7 Hz, 3H), 3.70-3.48 (m, 2H). c-306 ¹H NMR (600 MHz,CDCl₃) δ 8.49 (s, 1H), [M + H]⁺ 549.0 8.27 (s, 1H), 6.86 (s, 1H), 4.40-4.20 (m, 2H), 3.63 (d, J = 23.3 Hz, 3H), 3.53-3.31 (m, 2H), 1.25 (td, J= 7.1, 3.0 Hz, 3H). c-317 ¹H NMR (600 MHz, CDCl₃) δ 7.59-7.46 [M + H]⁺604.9 (m, 2H), 5.87 (tdt, J = 54.7, 23.8, 3.9 Hz, 1H), 4.33-4.14 (m,2H), 3.83 (d, J = 7.3 Hz, 3H), 3.60-3.37 (m, 2H). c-327 ¹H NMR (600 MHz,CDCl₃) δ 8.16 (d, [M + H]⁺ 516.0 J = 1.3 Hz, 1H), 7.50 (d, J = 1.2 Hz,1H), 6.84 (s, 1H), 4.11-3.99 (m, 2H), 3.81 (s, 3H), 3.48 (d, J = 2.2 Hz,2H), 1.16 (t, J = 7.1 Hz, 3H). c-346 ¹H NMR (600 MHz, CDCl₃) δ 8.58-8.43[M + H]⁺ 589.9 (m, 2H), 6.87 (s, 1H), 4.48-4.31 (m, 2H), 3.83 (d, J =6.7 Hz, 3H), 3.70-3.48 (m, 2H).

Hydrogen spectrum and mass spectrum data of nuclear magnetic resonanceof some compounds shown in the general formula (d) of Table 10 wereshown in Table 15.

TABLE 15 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance of Some Compounds Shown in General Formula (d) Com- pound¹H-NMR(600 MHz) MS (ESI) d-3 ¹H NMR (600 MHz, CDCl₃) δ 8.12 [M + H]⁺513.1 (s, 1H), 7.69 (s, 1H), 7.57 (brs, 1H), 3.75 (s, 3H), 3.67(s, 3H),3.36-3.29(m, 2H). d-7 ¹H NMR (600 MHz, CDCl₃) δ 8.01 [M + H]⁺ 497.1 (s,1H), 7.75 (s, 1H), 7.58 (brs, 1H), 3.71 (s, 3H), 3.70(s, 3H),3.35-3.29(m, 2H). d-8 ¹H NMR (600 MHz, CDCl₃) δ 7.91 [M + H]⁺ 562.0 (s,1H), 7.65 (s, 1H), 7.58 (brs, 1H), 3.74 (s, 3H), 3.60(s, 3H),3.24-3.06(m, 2H), 2.11(s, 3H). d-9 ¹H NMR (600 MHz, CDCl₃) δ 8.61 [M +H]⁺ 548.9 (brs, 2H), 7.61 (s, 1H), 7.55 (s, 1H), 7.54 (brs, 1H), 4.34(s, 2H), 3.73 (s, 3H), 3.61(s, 3H), 3.25-3.06(m, 2H). d-12 ¹H NMR (600MHz, CDCl₃) δ 8.13 [M + H]⁺ 559.1 (s, 1H), 7.57-7.49 (m, 1H), 7.35 (t, J= 2.2 Hz, 1H), 3.80 (d, J = 18.3 Hz, 3H), 3.61 (d, J = 35.5 Hz, 3H),3.56-3.37 (m, 2H), 2.92 (II, J = 11.8, 3.4 Hz, 1H), 2.07-1.98 (m, 2H),1.97-1.86 (m, 2H), 1.77-1.69 (m, 1H), 1.52-1.43 (m, 2H), 1.44-1.34 (m,3H). d-13 ¹H NMR (600 MHz, CDCl₃) δ 8.12 (s, 1H), [M + H]⁺ 491.1 7.55(s, 1H), 7.24 (d, J = 153.3 Hz, 1H), 3.82 (d, J = 16.2 Hz, 3H), 3.62 (d,J = 15.5 Hz, 3H), 3.48-3.36 (m, 1H), 3.45-3.29 (m, 1H), 2.99 (d, J =13.9 Hz, 3H). d-14 ¹H NMR (600 MHz, CDCl₃) δ 8.14 (s, 1H), [M + H]⁺505.0 7.57 (s, 1H), 7.40 (s, 1H), 3.80 (d, J = 16.4 Hz, 3H), 3.61 (d, J= 31.8 Hz, 3H), 3.51-3.40 (m, 1H), 3.46- 3.29 (m, 1H), 3.20-2.98 (m,2H), 1.38-1.29 (m, 3H). d-15 ¹H NMR (600 MHz, CDCl₃) δ 8.71-8.63 [M +H]⁺ 638.0 (m, 1H), 8.11 (s, 1H), 8.01 (dd, J = 18.1, 7.8 Hz, 1H), 7.95(qd, J = 7.5, 1.7 Hz, 1H), 7.60 (s, 1H), 7.52-7.48 (m, 1H), 7.43 (dddd,J = 20.7, 7.5, 4.7, 1.1 Hz, 1H), 4.26-4.07 (m, 2H), 4.07- 4.01 (m, 1H),3.69 (t, J = 6.8 Hz, 1H), 3.56-3.29 (m, 2H), 1.59 (dq, J = 14.0, 7.2 Hz,1H), 1.54-1.44 (m, 2H), 1.31-1.21 (m, 3H), 1.14 (ddd, J = 25.1, 15.4,8.0 Hz, 2H), 0.93-0.79 (m, 6H). d-17 ¹H NMR (600 MHz, CDCl₃) δ 8.07 [M +H]⁺ 671.0 (s, 1H), 7.78 (s, 2H), 7.52 (dt, J = 6.6, 2.3 Hz, 3H), 6.99(s, 1H), 4.14 (ddt, J = 45.1, 10.8, 6.8 Hz, 2H), 3.85 (t, J = 6.8 Hz,2H), 3.36 (s, 2H), 1.60-1.51 (m, 2H), 1.45-1.37 (m, 2H), 1.25-1.18 (m,4H), 0.86 (td, J = 7.4, 1.9 Hz, 6H). d-18 ¹H NMR (600 MHz, CDCl₃) δ 8.07(s, 1H), [M + H]⁺ 651.2 7.66 (s, 2H), 7.55-7.48 (m, 1H), 7.38-7.30 (m,3H), 4.22-4.10 (m, 2H), 4.09-3.99 (m, 1H), 3.84 (td, J = 6.8, 2.7 Hz,1H), 3.44 (d, J = 17.2 Hz, 1H), 3.32 (dd, J = 17.3, 8.4 Hz, 1H), 2.41(d, J = 7.6 Hz, 3H), 1.62-1.49 (m, 3H), 1.41-1.34 (m, 1H), 1.24- 1.15(m, 4H), 0.87-0.82 (m, 6H). d-20 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺529.9 (s, 1H), 7.46 (s, 1H), 7.45 (brs, 1H), 5.45 (brs, 2H), 3.62 (s,3H), 3.13-3.05(m, 2H). d-24 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺559.0 (s, 1H), 7.47 (s, 1H), 7.45 (brs, 1H), 3.64 (s, 3H), 3.62 (s, 3H),3.395 (dd, J = 3.4, 1.8 Hz, 1H), 1.12 (d, J = 2.8 Hz, 3H). d-27 ¹H NMR(600 MHz, CDCl₃) δ 8.16 [M + H]⁺ 612.9 (s, 1H), 7.42 (s, 1H), 7.54 (t, J= 2.3 Hz, 1H), 4.78-4.63 (m, 2H), 4.49-4.29 (m, 2H), 3.82 (d, J = 4.8Hz, 3H), 3.71-3.46 (m, 2H). d-33 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺529.0 (s, 1H), 7.46 (s, 1H), 7.45 (brs, 1H), 3.74 (s, 3H), 3.33-3.25(m,2H), 2.10 (s, 3H). d-34 ¹H NMR (600 MHz, CDCl₃) δ 8.16 [M + H]⁺ 564.9(s, 1H), 7.44 (s, 1H), 7.46 (brs, 1H), 3.72 (s, 3H), 3.13-3.05(m, 2H).d-35 H NMR (600 MHz, CDCl₃) δ 8.18 [M + H]⁺ 554.9 (s, 1H), 7.43 (s, 1H),7.45 (brs, 1H), 3.68 (s, 3H), 3.03-2.95(m, 2H). d-38 ¹H NMR (600 MHz,DMSO) δ 9.57 (d, [M + H]⁺ 545.0 J = 57.9 Hz, 1H), 8.18 (m, 2H), 4.29-4.16 (m, 2H), 3.55-3.46 (m, 2H), 1.15 (dt, J = 15.9, 7.1 Hz, 3H). d-42¹H NMR (600 MHz, CDCl₃) δ 8.16 [M + H]⁺ 694.9 (s, 1H), 7.41 (s, 1H),6.95 (brs, 1H), 5.69-5.59 (m, 1H), 3.85 (d, J = 21.5 Hz, 3H), 3.81-3.62(m, 2H). d-46 ¹H NMR (600 MHz, CDCl₃) δ 8.10 [M + H]⁺ 513.0 (s, 1H),7.44 (s, 1H), 7.46 (brs, 1H), 3.13-3.06(m, 2H), 2.43 (s, 3H), 2.10 (s,3H).. d-48 ¹H NMR (600 MHz, CDCl₃) δ 8.09 [M + H]⁺ 538.9 (s, 1H), 7.43(s, 1H), 7.40 (brs, 1H), 3.13-3.05(m, 2H), 2.40 (s, 3H). d-49 ¹H NMR(600 MHz, CDCl₃) δ 8.07 [M + H]⁺ 566.9 (s, 1H), 7.46 (s, 1H), 7.39 (brs,1H), 3.11-3.06(m, 2H), 2.39 (s, 3H). d-50 ¹H NMR (600 MHz, CDCl₃) δ 8.05[M + H]⁺ 620.9 (s, 1H), 7.46 (s, 1H), 7.45 (brs, 1H), 3.13-3.05(m, 2H).d-52 ¹H NMR (600 MHz, CDCl₃) δ 8.05 [M + H]⁺ 601.8 (s, 1H), 7.51 (s,1H), 7.44 (brs, 1H), 7.23-7.19(m, 5H), 3.33-3.25(m, 2H). d-54 ¹H NMR(600 MHz, CDCl₃) δ 8.08 [M + H]⁺ 582.8 (s, 1H), 7.50 (s, 1H), 7.45 (brs,1H), 3.74 (s, 3H), 3.33-3.25(m, 2H). d-60 ¹H NMR (600 MHz, CDCl₃) δ 8.05[M + H]⁺ 487.9 (s, 1H), 7.55 (s, 1H), 7.41 (brs, 1H), 3.11-3.02(m, 2H).d-63 ¹H NMR (600 MHz, CDCl₃) δ 8.07 [M + H]⁺ 602.8 (s, 1H), 7.56 (s,1H), 7.42 (brs, 1H), 3.31-3.22(m, 2H). d-64 ¹H NMR (600 MHz, CDCl₃) δ8.06 [M + H]⁺ 549.9 (s, 1H), 7.58 (s, 1H), 7.43 (brs, 1H), 3.15-3.07(m,2H). d-65 ¹H NMR (600 MHz, CDCl₃) δ 8.03 [M + H]⁺ 521.9 (s, 1H), 7.50(s, 1H), 7.41 (brs, 1H), 3.12-3.07(m, 2H). d-67 ¹H NMR (600 MHz, CDCl₃)δ 8.05 [M + H]⁺ 511.9 (s, 1H), 7.56 (s, 1H), 7.44 (brs, 1H), 3.61(s,3H), 3.33-3.25(m, 2H). d-69 ¹H NMR (600 MHz, CDCl₃) δ 8.03 [M + H]⁺565.1 (s, 1H), 7.47 (s, 1H), 7.20 (brs, 1H), 3.00-2.92(m, 2H). d-70 ¹HNMR (600 MHz, CDCl₃) δ 8.07 [M + H]⁺ 521.9 (s, 1H), 7.47 (s, 1H), 7.21(brs, 1H), 3.01-2.93(m, 2H). d-72 ¹H NMR (600 MHz, CDCl₃) δ 8.13 [M +H]⁺ 629.0 (s, 1H), 7.57 (s, 1H), 6.88 (s, 0H), 4.24- 4.19 (m, 2H),4.08-3.93 (m, 2H), 3.57-3.45 (m, 1H), 3.48-3.32 (m, 1H), 1.62-1.53 (m,2H), 1.50 (dddd, J = 13.7, 6.9, 3.5, 2.3 Hz, 2H), 1.31-1.19 (m, 4H),1.01-0.81 (m, 6H). d-73 ¹H NMR (600 MHz, CDCl₃) δ 8.12 (s, 1H), [M + H]⁺601.0 7.57 (s, 1H), 6.85 (s, 1H), 5.11 (tt, J = 12.5, 6.2 Hz, 1H), 4.93(dp, J = 30.3, 6.3 Hz, 1H), 3.53-3.37 (m, 1H), 3.45-3.22 (m, 1H),1.27-1.20 (m, 6H), 1.18-1.07 (m, 6H). d-74 ¹H NMR (600 MHz, CDCl₃) δ8.15 (s, [M + H]⁺ 486.9 1H), 7.56 (s, 1H), 7.45 (brs, 1H), 4.75 (s, 1H),3.65(s, 3H). d-81 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 510.9 (s, 1H),7.58 (s, 1H), 7.47 (brs, 1H), 4.75 (s, 1H). d-82 ¹H NMR (600 MHz, CDCl₃)δ 8.16 [M + H]⁺ 439.9 (s, 1H), 7.50 (s, 1H), 7.49 (brs, 1H), 4.76 (s,1H). d-85 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 497.1 (s, 1H), 7.66(s, 1H), 7.45 (brs, 1H), 3.74 (d, J = 6.9 Hz, 1H), 2.33-2.25(m, 2H).d-90 ¹H NMR (600 MHz, CDCl₃) δ 8.18 [M + H]⁺ 448.9 (s, 1H), 7.61 (s,1H), 7.39 (brs, 1H), 4.71 (s, 1H). d-98 ¹H NMR (600 MHz, CDCl₃) δ 8.15(s, 1H), [M + H]⁺ 530.1 7.56 (s, 1H), 7.35 (brs, 1H), 4.74 (s, 1H),3.65(s, 3H), 3.31-3.25(m, 2H). d-103 ¹H NMR (600 MHz, CDCl₃) δ 8.18 [M +H]⁺ 567.9 (s, 1H), 7.56 (s, 1H), 7.35 (brs, 1H), 4.74 (s, 1H),3.33-3.25(m, 2H). d-107 ¹H NMR (600 MHz, CDCl₃) δ 8.20 [M + H]⁺ 525.9(s, 1H), 7.50 (s, 1H), 7.41 (brs, 1H), 4.65 (s, 1H). d-109 ¹H NMR (600MHz, CDCl₃) δ 8.17 [M + H]⁺ 514.9 (s, 1H), 7.56 (s, 1H), 7.45 (brs, 1H),7.35 (brs, 1H), 4.74 (s, 1H), 2.75(s, 3H). d-112 ¹H NMR (600 MHz, CDCl₃)δ 8.17 [M + H]⁺ 499.9 (s, 1H), 7.56 (s, 1H), 7.35 (brs, 1H), 4.74 (s,1H), 2.45(s, 3H). d-114 ¹H NMR (600 MHz, CDCl₃) δ 8.20 [M + H]⁺ 535.8(s, 1H), 7.56 (s, 1H), 7.35 (brs, 1H), 4.14 (s, 1H). d-119 ¹H NMR (600MHz, CDCl₃) δ 8.19 [M + H]⁺ 497.8 (s, 1H), 7.58 (s, 1H), 7.44 (brs, 1H),6.23(d, J = 8.3 Hz, 1H), 6.02(dd, J = 1.3, 8.4 Hz, 1H), 4.81 (s, 1H),1.63(d, J = 9.2 Hz, 3H). d-122 ¹H NMR (600 MHz, CDCl₃) δ 8.23 [M + H]⁺468.9 (s, 1H), 7.67 (s, 1H), 7.44 (brs, 1H), 4.81 (dd, J = 1.3, 8.4 Hz,1H), 3.81 (s, 3H), 2.82 (m, 1H), 1.13(d, J = 10.2 Hz, 3H). d-127 ¹H NMR(600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 478.9 (s, 1H), 7.54 (s, 1H), 7.43 (brs,1H), 4.74 (s, 1H). d-129 ¹H NMR (600 MHz, CDCl₃) δ 8.16 [M + H]⁺ 421.9(s, 1H), 7.49 (s, 1H), 7.43 (brs, 1H), 3.74 (s, 1H), 3.13-3.05(m, 2H).d-133 ¹H NMR (600 MHz, CDCl₃) δ 8.16 [M + H]⁺ 453.9 (s, 1H), 7.53 (brs,1H), 7.49 (s, 1H), 7.43 (brs, 1H), 4.14 (s, 1H), 3.34 (s, 3H),3.13-3.05(m, 2H). d-141 ¹H NMR (600 MHz, CDCl₃) δ 8.15 [M + H]⁺ 424.9(s, 1H), 7.43 (s, 1H), 7.43 (brs, 1H), 3.74 (d, J = 8.4 Hz, 1H),2.04-1.96 (m, 1H), 0.98 (d, J = 12.9 Hz, 6H).

Hydrogen spectrum and mass spectrum data of nuclear magnetic resonanceof some compounds shown in the general formula (e) of Table 11 wereshown in Table 16.

TABLE 16 Hydrogen Spectrum and Mass Spectrum Data of Nuclear MagneticResonance of Some Compounds Shown in General Formula (e) Com- pound¹H-NMR(600 MHz) MS (ESI) e-1 ¹H NMR (600 MHz, CDCl₃) δ 8.15 (dd, [M +H]⁺ 545.1 J = 5.3, 1.8 Hz, 1H), 7.58 (d, J = 1.7 Hz, 1H), 7.15 (brs,1H), 3.82 (s, 3H), 3.64 (s, 3H), 3.57-3.25 (m, 2H). e-2 ¹H NMR (600 MHz,CDCl₃) δ 8.13 [M + H]⁺ 559.0 (d, J = 1.3 Hz, 1H), 7.57 (d, J = 1.2 Hz,1H), 6.84 (brs, 1H), 4.11-3.99 (m, 2H), 3.81 (s, 3H), 3.48 (d, J = 2.2Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H). e-3 ¹H NMR (600 MHz, CDCl₃) δ 8.36[M + H]⁺ 612.9 (s, 1H), 7.62 (s, 1H), 7.54 (t, J = 2.3 Hz, 1H),4.78-4.63 (m, 2H), 4.49-4.29 (m, 2H), 3.82 (d, J = 4.8 Hz, 3H),3.71-3.46 (m, 2H). e-4 ¹H NMR (600 MHz, CDCl₃) δ 8.34 [M + H]⁺ 594.9 (s,1H), 7.64 (s, 1H), 6.92 (brs, 1H), 5.87 (tdt, J = 54.7, 24.2, 3.9 Hz,1H), 4.35-4.12 (m, 2H), 3.83 (s, 3H), 3.63-3.35 (m, 2H). e-5 ¹H NMR (600MHz, CDCl₃) δ 8.25 [M + H]⁺ 573.2 (m, 1H), 7.67 (s, 1H), 7.27 (brs, 1H),4.38-4.21 (m, 2H), 4.15-4.00 (m, 2H), 3.69-3.30 (m, 2H), 1.25 (td, J =7.1, 1.4 Hz, 3H), 1.17 (dt, J = 16.7, 7.1 Hz, 3H). e-6 ¹H NMR (600 MHz,CDCl₃) δ 8.23 (dd, [M + H]⁺ 559.0 J = 4.9, 1.8 Hz, 1H), 7.67 (d, J = 1.8Hz, 1H), 6.86 (brs, 1H), 4.40-4.20 (m, 2H), 3.63 (s, 3H), 3.53-3.31 (m,2H), 1.25 (td, J = 7.1, 3.0 Hz, 3H). e-7 ¹H NMR (600 MHz, CDCl₃) δ 8.17(dd, [M + H]⁺ 545.1 J = 5.3, 1.8 Hz, 1H), 7.59 (d, J = 1.7 Hz, 1H), 7.16(brs, 1H), 3.83 (s, 3H), 3.65 (s, 3H), 3.57-3.25 (m, 2H). e-8 ¹H NMR(600 MHz, CDCl₃) δ 8.13 [M + H]⁺ 559.0 (d, J = 1.3 Hz, 1H), 7.55 (d, J =1.2 Hz, 1H), 6.82 (brs, 1H), 4.11-3.97 (m, 2H), 3.81 (s, 3H), 3.49 (d, J= 2.2 Hz, 2H), 1.16 (t, J = 7.2 Hz, 3H). e-9 ¹H NMR (600 MHz, CDCl₃) δ8.35 (s, 1H), [M + H]⁺ 612.9 7.63 (s, 1H), 7.44 (t, J = 2.3 Hz, 1H),4.78-4.62 (m, 2H), 4.50-4.29 (m, 2H), 3.82 (d, J = 4.8 Hz, 3H),3.71-3.46 (m, 2H). e-10 ¹H NMR (600 MHz, CDCl₃) δ 8.34 [M + H]⁺ 594.9(s, 1H), 7.64 (s, 1H), 6.96 (brs, 1H), 5.87 (tdt, J = 54.7, 24.2, 3.9Hz, 1H), 4.35-4.12 (m, 2H), 3.93 (s, 3H), 3.64-3.35 (m, 2H). e-11 ¹H NMR(600 MHz, CDCl₃) δ 8.25 [M + H]⁺ 573.2 (m, 1H), 7.67 (s, 1H), 7.27 (brs,1H), 4.39-4.21 (m, 2H), 4.15-4.01 (m, 2H), 3.68-3.30 (m, 2H), 1.25 (td,J = 7.1, 1.5 Hz, 3H), 1.17 (dt, J = 16.7, 7.2 Hz, 3H). e-12 ¹H NMR (600MHz, CDCl₃) δ 8.22 [M + H]⁺ 559.0 (dd, J = 4.9, 1.8 Hz, 1H), 7.68 (d, J= 1.8 Hz, 1H), 6.96 (brs, 1H), 4.40-4.20 (m, 2H), 3.63 (s, 3H),3.53-3.31 (m, 2H), 1.25 (td, J = 7.1, 3.1 Hz, 3H). e-13 ¹H NMR (600 MHz,CDCl₃) δ 8.16 (dd, [M + H]⁺ 545.1 J = 5.3, 1.9 Hz, 1H), 7.58 (d, J = 1.8Hz, 1H), 7.13 (brs, 1H), 3.82 (s, 3H), 3.64 (s, 3H), 3.59-3.25 (m, 2H).e-14 ¹H NMR (600 MHz, CDCl₃) δ 8.11 (d, [M + H]⁺ 559.0 J = 1.4 Hz, 1H),7.47 (d, J = 1.2 Hz, 1H), 6.84 (brs, 1H), 4.11-3.99 (m, 2H), 3.83 (s,3H), 3.48 (d, J = 2.2 Hz, 2H), 1.16 (t, J = 7.5 Hz, 3H). e-15 ¹H NMR(600 MHz, CDCl₃) δ 8.32 [M + H]⁺ 612.9 (s, 1H), 7.62 (s, 1H), 7.54 (t, J= 2.4 Hz, 1H), 4.78-4.63 (m, 2H), 4.49-4.29 (m, 2H), 3.81 (d, J = 4.8Hz, 3H), 3.71-3.46 (m, 2H). e-16 ¹H NMR (600 MHz, CDCl₃) δ 8.33 [M + H]⁺594.9 (s, 1H), 7.64 (s, 1H), 6.92 (brs, 1H), 5.87 (tdt, J = 54.7, 24.2,3.9 Hz, 1H), 4.34-4.12 (m, 2H), 3.83 (s, 3H), 3.64-3.35 (m, 2H). e-17 ¹HNMR (600 MHz, CDCl₃) δ 8.26 [M + H]⁺ 573.2 (m, 1H), 7.67 (s, 1H), 7.27(brs, 1H), 4.40-4.21 (m, 2H), 4.15-4.01 (m, 2H), 3.69-3.30 (m, 2H), 1.25(td, J = 7.3, 1.2Hz, 3H), 1.17 (dt, J = 16.7, 7.3 Hz, 3H). e-18 ¹H NMR(600 MHz, CDCl₃) δ 8.33 (dd, [M + H]⁺ 559.0 J = 4.9, 1.9 Hz, 1H), 7.68(d, J = 1.6 Hz, 1H), 6.86 (brs, 1H), 4.41-4.21 (m, 2H), 3.62 (s, 3H),3.52-3.30 (m, 2H), 1.24 (td, J = 7.0, 3.0 Hz, 3H). e-19 ¹H NMR (600 MHz,CDCl₃) δ 8.20 (s, 1H), [M + H]⁺ 545.1 7.77 (s, 1H), 7.05 (brs, 1H), 3.82(s, 3H), 3.64 (s, 3H), 3.57-3.25 (m, 2H). e-20 ¹H NMR (600 MHz, CDCl₃) δ8.23 (s, 1H), [M + H]⁺ 545.1 7.77 (s, 1H), 6.84 (brs, 1H), 4.11- 3.99(m, 2H), 3.81 (s, 3H), 3.48 (d, J = 2.2 Hz, 2H), 1.16 (t, J = 7.1 Hz,3H). e-21 ¹H NMR (600 MHz, CDCl₃) δ 8.26 [M + H]⁺ 559.0 (s, 1H), 7.87(s, 1H), 7.54 (t, J = 2.3 Hz, 1H), 4.78-4.63 (m, 2H), 4.49-4.29 (m, 2H),3.82 (s, 3H), 3.71- 3.46 (m, 2H). e-22 ¹H NMR (600 MHz, CDCl₃) δ 8.34(s, 1H), [M + H]⁺ 612.9 7.69 (s, 1H), 6.92 (brs, 1H), 5.87 (tdt, J =54.7, 24.2, 3.9 Hz, 1H), 4.35-4.12 (m, 2H), 3.83 (s, 3H), 3.63-3.35 (m,2H). e-23 ¹H NMR (600 MHz, CDCl₃) δ 8.25 [M + H]⁺ 594.9 (s, 1H), 7.57(s, 1H), 7.27 (brs, 1H), 4.38- 4.21 (m, 2H), 4.15-4.00 (m, 2H),3.69-3.30 (m, 2H), 1.25 (td, J = 7.1, 1.4 Hz, 3H), 1.17 (dt, J = 16.7,7.1 Hz, 3H). e-24 ¹H NMR (600 MHz, CDCl₃) δ 8.23 (s, 1H), [M + H]⁺ 573.27.88 (s, 1H), 6.86 (s, 1H), 4.40- 4.20 (m, 2H), 3.63 (s, 3H), 3.53-3.31(m, 2H), 1.25 (td, J = 7.1, 3.0 Hz, 3H).

Embodiment 9: Insecticidal Activity Embodiment

(1) Insecticidal Activity on 2^(nd)-Instar Larvae of Plutellaxylostella.

Plutella xylostella (L.) is a lepidoptera pest with a chewing mouthpartand is a common vegetable pest. The 2^(nd)-instar larvae of Plutellaxylostella were used as test objects and tested by using a leafimmersion feeding method.

Operation process: Samples were weighed accurately, and respectivelyadded with 200 μL of dimethyl sulfoxide to prepare 10 g/L mother liquorwhich was diluted into a concentration of 500 ppm with an aqueoussolution containing 0.05% of Tween-80 during the test. A hole puncherwith a diameter of 1.0 cm was used to make cleaned cabbage leaves intoleaf discs. The leaf discs were immersed in a liquid medicine, taken outafter 5 seconds, air-dried naturally, and transferred into a cleanvessel. About 35 2^(nd)-instar larvae of Plutella xylostella were putinto the vessel and fed at a constant temperature of 28° C. Eachconcentration was repeated 3 times, and an aqueous solution containing0.05% of Tween-80 was used as a control group. After being treated for24 hours, a number of dead Plutella xylostella was counted, and amortality (%) was calculated according to a formula that mortality(%)=(number of live larvae in the control group—number of treated livelarvae)/number of live larvae in the control group*100%. The resultswere shown in Table 17 to Table 24.

(2) Insecticidal Activity on 2n^(d)-Instar Larvae of Spodoptera exigua.

Spodoptera exigua is a lepidoptera pest with a chewing mouthpart and isa common vegetable pest. The 2n^(d)-instar larvae of Spodoptera exiguawere used as test objects and tested by using a leaf immersion feedingmethod.

Operation process: Samples were weighed accurately, and respectivelyadded with 200 μL of dimethyl sulfoxide to prepare 10 g/L mother liquorwhich was diluted into a concentration of 500 ppm with an aqueoussolution containing 0.05% of Tween-80 during the test. A hole puncherwith a diameter of 1.0 cm was used to make cleaned cabbage leaves intoleaf discs. The leaf discs were immersed in a liquid medicine, taken outafter 5 seconds, air-dried naturally, and transferred into a cleanvessel. About 35 2^(nd)-instar larvae of Spodoptera exigua were put intothe vessel and fed at a constant temperature of 28° C. Eachconcentration was repeated 3 times, and an aqueous solution containing0.05% of Tween-80 was used as a control group. After being treated for24 hours, a number of dead Plutella xylostella was counted, and amortality (%) was calculated according to a formula that mortality(%)=(number of live larvae in the control group—number of treated livelarvae)/number of live larvae in the control group*100%. The resultswere shown in Table 17 to Table 24.

(3) Insecticidal Activity on Aphid Adults.

Aphid is a homoptera pest with a piercing-sucking mouthpart and is acommon vegetable pest. Aphis craccivora were taken as test objects andtested by using an impregnation method.

Operation process: Samples were weighed accurately, and respectivelyadded with 200 μL of dimethyl sulfoxide to prepare 10 g/L mother liquorwhich was diluted into a concentration of 500 ppm with an aqueoussolution containing 0.05% of Tween-80 during the test. After thewingless Aphis craccivora adults stably sucked on bean sprouts, thewingless Aphis craccivora adults together with the bean sprouts wereimmersed into a liquid medicine with a concentration of 500 ppm, takenout after 5 seconds, air-dried naturally, transferred into a cleanvessel, and fed at a constant temperature of 23° C. Each concentrationwas repeated 3 times, and an aqueous solution containing 0.05% ofTween-80 was used as a control group. After being treated for 24 hours,a number of dead Aphis craccivora was counted, and a mortality (%) wascalculated according to a formula that mortality (%)=(number of liveAphis craccivora in the control group−number of treated live Aphiscraccivora)/number of live Aphis craccivora in the control group*100%.The results were shown in Table 17 to Table 24.

(4) Insecticidal Activity on Solenopsis invicta.

As a hymenoptera pests and a social insect, Solenopsis invicta is one ofthe most destructive invasive organisms. Solenopsis invicta were used astest objects and tested by using a water test tube poison-feedingmethod.

Operation process: Samples were weighed accurately, and respectivelyadded with 200 μL of dimethyl sulfoxide to prepare 10 g/L mother liquorwhich was diluted into a concentration of 100 ppm with a mixed aqueoussolution containing 0.05% of Tween-80 and 5% of honey during the test.Solenopsis invicta were placed in a raising test tube, and a liquidmedicine was injected into a silica gel plug of the raising test tube bya syringe as long as the liquid medicine did not seep out. The raisingtest tube was placed in a raising box horizontally, and a small amountof ham sausages were added to the raising test tube as food to raise theSolenopsis invicta at a constant temperature of 25° C. After beingtreated for 24 hours and 72 hours, a number of live Solenopsis invictaand a number of dead Solenopsis invicta were counted, and a mortality(%) was calculated according to a formula that mortality (%)=(number oflive Solenopsis invicta in the control group−number of treated liveSolenopsis invicta)/number of live Solenopsis invicta in the controlgroup*100%. The results were shown in Table 17 to Table 24.

TABLE 17 Insecticidal Activity of Compounds of Formula (I) on Test PestsInsecticidal activity Plutella Spodoptera Aphis xylostella exiguacraccivora Solenopsis Mortality Mortality Mortality invicta Com- (%) (%)(%) Mortality (%) pound 500 500 500 100 ppm No. ppm ppm ppm 24 h 72 h A195 90 100 20 87 A2 97 100 100 19 93 A3 90 100 100 25 100 A4 86 100 10020 87 A5 100 100 100 34 100 A6 100 100 100 44 100 A7 100 100 100 20 100A8 100 90 100 26 93 A9 100 100 100 24 100 A10 86 100 100 20 87 A11 100100 100 34 100 A12 100 100 100 44 100 A13 100 100 100 20 100 A14 100 90100 26 93 A15 100 100 100 24 100 A16 86 100 100 20 87 A17 100 100 100 34100 A18 100 100 100 44 100 A19 100 100 100 20 100 A20 100 90 100 26 93A21 100 100 100 24 100 A22 96 100 100 30 97 A23 100 100 100 34 100 A24100 100 100 44 100 A25 100 100 100 38 100 A26 100 100 100 45 100 A27 100100 100 30 100 A28 100 90 100 29 97 A29 100 100 100 26 95 A30 100 100100 40 100 A31 100 100 100 20 100 A32 100 90 100 26 93 A33 100 100 10024 100 A34 96 100 100 28 97 A35 100 100 100 31 99 A36 100 100 100 44 100A37 100 100 100 20 100 A38 100 90 100 26 93 A39 100 100 100 24 100 A4096 100 100 20 97 A41 100 100 100 24 100 A42 100 100 100 44 100 A43 100100 100 20 100 A44 100 90 100 26 93 A45 100 100 100 24 100 A46 86 100100 20 87 A47 100 100 100 34 100

TABLE 18 Insecticidal Activity of Some Compounds of Formula (I) on TestPests Insecticidal activity Plutella Spodoptera Aphis xylostella exiguacraccivora Solenopsis Mortality Mortality Mortality invicta Com- (%) (%)(%) Mortality (%) pound 500 500 500 100 ppm No. ppm ppm ppm 24 h 72 h B1100 100 100 20 100 B2 100 90 93 26 93 B3 100 100 100 24 100 B4 86 100100 20 88 B5 100 100 100 34 100 B6 90 100 100 44 100 B7 100 100 100 38100 B8 100 100 100 45 100 B9 100 100 100 38 100 B10 100 95 100 30 90 B11100 100 100 33 95 B12 100 100 100 40 100

TABLE 19 Insecticidal Activity of Compounds of Formula (I) in Table 3 onTest Pests Insecticidal activity Plutella Spodoptera Aphis xylostellaexigua craccivora Solenopsis Mortality Mortality Mortality invicta Com-(%) (%) (%) Mortality (%) pound 500 500 500 100 ppm No. ppm ppm ppm 24 h72 h C1 89 100 100 20 100 C2 100 90 100 26 93 C3 100 100 100 24 100 C486 76 100 20 87 C5 100 100 100 34 100 C6 100 100 100 44 100 C7 100 100100 38 100 C8 91 85 95 36 92 C9 100 100 100 39 100 C10 100 85 100 27 100C11 100 100 100 46 100 C12 100 91 100 18 95 C13 100 100 100 32 100 C14100 100 100 30 100 C15 89 100 100 29 90 C16 100 95 99 23 89 C17 88 89100 15 68 C18 90 86 98 20 70 C19 90 90 100 18 70 C20 100 100 100 28 99C21 90 95 100 19 99 C22 99 94 89 20 70 C23 86 88 95 18 80 C24 100 100100 36 100 C25 92 97 86 25 71 C26 89 90 100 20 80 C27 76 86 100 27 86C28 100 100 100 30 98 C29 100 93 100 30 100 C30 100 90 92 24 100 C31 100100 100 34 100 C32 100 90 95 25 100 C33 100 100 100 36 100 C34 100 100100 40 100 C35 100 100 100 38 100 C36 90 90 100 10 90 C37 100 100 100 20100 C38 100 90 100 25 90 C39 90 100 98 24 87 C40 100 95 100 28 90 C41 8994 100 19 90 C42 91 94 100 20 70 C43 86 89 95 18 80 C44 90 100 100 36 90C45 93 97 86 25 71 C46 89 91 90 21 80 C47 77 86 80 27 87 C48 76 85 79 2686 C49 87 89 90 20 81 C50 81 86 90 26 86 C51 87 85 79 19 86 C52 90 91100 22 90 C53 78 89 90 28 97 C54 77 78 87 17 84 C55 88 80 91 19 83 C5682 87 91 27 80 C57 78 76 80 20 89 C58 100 100 100 29 98 C59 100 90 10029 100 C60 90 92 100 25 92 C61 88 100 90 28 100 C62 80 85 97 27 100 C6398 90 96 29 98 C64 92 97 100 17 90

TABLE 20 Insecticidal Activity of Some Compounds of General Formula (a)on Test Pests Insecticidal activity Plutella Spodoptera Aphis xylostellaexigua craccivora Solenopsis Mortality Mortality Mortality invicta (%)(%) (%) Mortality (%) Com- 500 500 500 100 ppm pound ppm ppm ppm 24 h 72h a-1 100 100 100 20 100 a-2 97 97 100 19 98 a-3 90 90 100 25 100 a-4 8695 100 20 97 a-5 90 89 100 24 96 a-6 100 100 100 34 100 a-7 95 91 100 2090 a-8 95 90 95 10 90 a-9 100 100 100 14 100 a-10 100 100 100 20 97 a-11100 100 100 24 100 a-12 100 100 100 19 100 a-13 100 100 100 20 100 a-14100 100 100 26 100 a-15 100 100 100 21 100 a-16 96 86 100 20 87 a-17 9689 100 24 90 a-18 96 86 100 20 87 a-19 95 91 100 20 90 a-20 100 90 10026 93 a-21 91 79 100 24 90 a-22 100 100 100 30 100 a-26 100 100 100 34100 a-27 100 100 100 25 100 a-28 100 95 100 23 99 a-29 100 91 100 14 96a-30 96 90 100 20 97 a-36 100 96 100 14 91 a-37 100 96 100 15 99 a-38 9090 100 26 100 a-39 90 89 100 25 93 a-40 90 89 100 19 90 a-41 86 81 99 2094 a-42 96 96 100 21 96 a-43 86 81 99 20 94 a-44 100 95 100 15 95 a-45100 91 100 20 90 a-47 100 90 100 19 97 a-51 91 89 100 16 95 a-52 100 8991 20 89 a-53 100 96 100 20 100 a-56 100 90 100 16 93 a-57 100 100 10024 100 a-59 96 91 100 28 97 a-62 100 100 100 21 99 a-63 100 100 100 24100 a-64 100 99 100 20 99 a-65 100 100 100 26 100 a-71 100 99 100 24 100a-72 96 89 100 20 91 a-76 95 85 91 24 80 a-77 90 86 96 44 90 a-80 91 85100 10 100 a-83 100 90 100 26 93 a-86 100 89 100 24 89 a-87 96 100 10020 97 a-88 100 100 100 34 100 a-95 96 89 100 21 92 a-100 91 90 100 20 90a-109 95 89 100 20 90 a-111 100 100 100 19 97 a-112 100 96 100 16 99a-118 96 95 100 25 100 a-122 91 89 100 20 90 a-132 90 90 100 26 94 a-133100 100 100 24 100 a-134 100 100 100 27 100 a-136 100 100 100 11 100

TABLE 21 Insecticidal Activity of Some Compounds of General Formula (b)on Test Pests Insecticidal activity Plutella Spodoptera Aphis xylostellaexigua craccivora Solenopsis Mortality Mortality Mortality invicta (%)(%) (%) Mortality (%) Com- 500 500 500 100 ppm pound ppm ppm ppm 24 h 72h b-1 100 100 100 20 97 b-2 100 95 100 19 93 b-3 90 90 95 25 90 b-4 9089 96 20 90 b-5 89 80 100 14 100 b-6 100 100 100 20 100 b-7 100 90 10017 97 b-8 100 96 100 26 92 b-9 100 100 100 19 100 b-10 100 100 100 20100 b-11 100 100 100 34 100 b-12 100 100 100 14 100 b-13 100 100 100 20100 b-14 100 100 100 26 100 b-15 100 100 100 24 100 b-16 96 90 100 20 97b-17 100 92 100 14 100 b-18 99 89 98 14 100 b-19 100 95 100 20 100 b-20100 90 100 21 93 b-21 90 81 90 24 86 b-23 96 95 100 10 97 b-25 100 100100 26 100 b-27 91 89 100 19 100 b-28 100 99 100 16 100 b-30 90 85 10025 94 b-34 90 87 100 10 100 b-37 86 90 99 20 94 b-38 90 85 99 32 90 b-3996 85 97 24 90 b-43 89 80 89 19 90 b-47 95 85 100 18 90 b-48 100 89 10015 90 b-50 99 90 100 10 100 b-54 100 90 100 25 97 b-56 100 100 100 26100 b-57 100 100 100 30 100 b-59 100 100 100 20 100 b-62 100 96 100 2693 b-63 100 100 100 24 100 b-66 96 91 100 28 97 b-68 99 100 100 21 99b-70 100 95 100 44 100 b-73 89 85 100 20 90 b-76 95 90 100 26 93 b-80 9590 100 14 90 b-86 96 89 100 20 97 b-87 95 95 100 14 100 b-88 100 100 10025 100 b-94 100 90 100 20 100 b-96 100 93 100 26 98 b-99 91 85 100 24 90b-104 96 96 100 20 96 b-111 100 100 100 24 100 b-116 100 98 100 20 100b-118 99 91 100 14 99 b-123 99 95 100 24 100 b-131 95 95 100 11 100b-134 100 100 100 26 100 b-135 100 100 100 23 100 b-136 100 100 100 2097 b-138 100 100 100 14 100

TABLE 22 Insecticidal Activity of Some Compounds of General Formula (c)on Test Pests Insecticidal activity Plutella Spodoptera Aphis xylostellaexigua craccivora Solenopsis Mortality Mortality Mortality invicta (%)(%) (%) Mortality (%) Com- 500 500 500 100 ppm pound ppm ppm ppm 24 h 72h c-2 95 90 100 20 97 c-4 97 100 100 29 93 c-7 100 100 100 20 100 c-8100 100 100 20 100 c-9 99 100 100 14 100 c-10 99 95 100 24 100 c-13 10095 100 21 100 c-14 100 96 100 26 100 c-15 95 90 100 24 100 c-19 100 100100 20 100 c-20 100 100 100 14 100 c-34 100 100 100 34 100 c-36 92 90 9521 100 c-37 96 90 100 21 93 c-39 95 89 100 24 90 c-42 86 80 100 20 97c-47 90 89 100 35 99 c-49 100 95 100 44 100 c-53 100 96 100 20 100 c-54100 90 100 26 96 c-57 95 89 100 24 95 c-61 96 100 100 26 97 c-64 96 90100 14 100 c-67 100 100 100 25 100 c-72 100 90 100 23 99 c-73 100 100100 14 90 c-77 96 90 100 20 97 c-80 100 100 100 13 90 c-84 99 96 100 2595 c-86 100 99 100 16 100 c-91 90 82 100 25 94 c-93 90 89 100 30 100c-96 86 90 99 20 84 c-97 100 100 100 32 100 c-98 96 90 100 24 90 c-10189 80 100 19 99 c-105 96 100 100 25 100 c-106 99 95 100 27 100 c-107 9990 100 26 99 c-110 100 100 100 14 100 c-111 98 99 100 17 99 c-113 98 9199 14 98 c-114 96 89 100 18 100 c-117 100 100 100 25 100 c-118 95 85 10020 90 c-121 100 90 100 19 97 c-123 100 96 100 26 99 c-126 100 100 100 35100 c-128 91 89 100 20 90 c-131 90 84 92 26 94 c-135 90 79 96 24 89c-139 96 91 100 28 87 c-145 100 95 100 11 99 c-149 100 100 100 31 100c-150 95 87 91 20 90 c-152 100 89 100 16 93 c-154 89 71 91 24 80 c-15996 100 100 20 97 c-164 100 80 100 24 90 c-166 100 100 100 25 100 c-169100 100 100 20 99 c-173 95 90 100 25 93 c-180 95 82 100 21 91 c-186 8981 99 20 87 c-188 100 100 100 14 100 c-196 100 90 100 20 97 c-203 97 100100 29 100 c-210 100 100 100 20 100 c-217 100 100 100 20 100 c-221 99100 100 14 100 c-224 99 95 100 25 100 c-231 100 100 100 21 100 c-238 10096 100 26 100 c-245 95 94 100 14 100 c-253 96 100 100 20 97 c-258 100100 100 14 100 c-262 100 100 100 34 100 c-266 92 90 95 21 100 c-273 9690 100 21 93 c-286 95 89 100 24 90 c-306 96 80 100 20 97 c-317 90 89 10020 100 c-327 100 95 100 34 100 c-346 100 96 100 20 100

TABLE 23 Insecticidal Activity of Some Compounds of General Formula (d)on Test Pests Insecticidal activity Plutella Spodoptera Aphis xylostellaexigua craccivora Solenopsis Mortality Mortality Mortality invicta (%)(%) (%) Mortality (%) Com- 500 500 500 100 ppm pound ppm ppm ppm 24 h 72h d-3 100 98 100 21 87 d-7 100 100 100 20 99 d-8 85 82 90 15 65 d-9 8279 96 21 77 d-10 55 50 90 34 80 d-11 76 70 99 14 76 d-12 86 96 100 20100 d-13 82 81 99 26 89 d-14 90 89 100 24 100 d-15 96 100 100 19 97 d-1685 93 96 34 100 d-17 99 95 100 42 100 d-18 81 80 100 15 85 d-19 100 90100 23 99 d-20 100 100 100 14 100 d-26 100 100 100 20 100 d-27 100 100100 14 100 d-28 100 96 100 25 100 d-33 100 99 100 26 100 d-34 90 95 10025 93 d-35 90 89 100 30 100 d-38 86 9 99 30 84 d-42 100 100 100 31 100d-46 95 90 100 14 90 d-47 100 100 100 29 99 d-48 96 90 100 26 100 d-49100 100 100 29 100 d-50 100 90 100 26 93 d-52 100 100 100 24 100 d-54100 99 100 21 99 d-56 90 89 99 14 80 d-57 89 80 90 20 70 d-58 76 70 9621 99 d-60 96 90 90 24 90 d-63 100 95 100 20 90 d-64 100 90 100 26 93d-65 100 100 100 24 90 d-67 100 90 100 41 99 d-69 90 86 100 44 100 d-7091 90 99 20 98 d-72 90 85 99 26 76 d-73 81 66 96 24 85 d-74 100 100 10021 99 d-77 100 99 100 44 100 d-81 99 90 100 35 100 d-82 95 89 100 25 90d-85 100 100 100 30 100 d-86 100 90 100 29 97 d-90 82 80 90 16 85 d-9489 90 99 20 90 d-98 100 100 100 20 99 d-103 100 98 100 26 93 d-107 100100 100 24 100 d-109 96 85 99 28 85 d-112 96 80 100 36 99 d-114 100 87100 24 90 d-115 99 90 100 20 100 d-119 89 90 92 26 83 d-122 91 84 90 2495 d-127 96 100 100 20 97 d-129 95 100 100 24 100 d-133 70 86 100 21 95d-141 90 95 100 11 91

TABLE 24 Insecticidal Activity of Some Compounds of General Formula (e)on Test Pests Insecticidal activity Plutella Spodoptera Aphis xylostellaexigua craccivora Solenopsis Mortality Mortality Mortality invicta (%)(%) (%) Mortality (%) Com- 500 500 500 100 ppm pound ppm ppm ppm 24 h 72h e-1 100 100 100 33 100 e-2 100 100 100 25 100 e-3 100 95 100 20 98 e-4100 100 100 32 100 e-5 100 100 100 34 100 e-6 100 100 100 34 100 e-7 100100 100 29 99 e-8 100 100 100 35 100 e-9 96 90 100 40 96 e-10 100 100100 37 100 e-11 100 100 100 33 100 e-12 100 100 100 34 100 e-13 100 100100 20 100 e-14 100 100 100 34 100 e-15 90 89 100 32 100 e-16 100 100100 32 99 e-17 100 100 100 30 100 e-18 100 100 100 29 100 e-19 100 100100 31 90 e-20 100 100 100 31 100 e-21 100 100 100 30 100 e-22 100 100100 35 100 e-23 100 100 100 34 93 e-24 100 100 100 34 100

It can be seen from the tables that the compounds illustrated in thepresent invention have a high killing activity on agroforestry pests,animal parasitic pests, sanitary insect pest and the like, have an goodactivity on lepidoptera, homoptera, hymenoptera pests and the like, havea delayed working effect on Solenopsis invicta, and have a betterkilling effect on a whole Solenopsis invicta nest and a queen Solenopsisinvicta.

Embodiment 10: Environmental Safety Embodiment

Results of toxicity tests of some compounds of the present invention onenvironmental non-target organisms were shown in the table below:

(1) Toxicity Test on 2^(nd)-Instar Larvae of Bombyx mori L.

Bombyx mori L. is an important economic insect sensitive to pesticidesin an agricultural ecosystem, and is also one of the non-targetorganisms of environmental ecology listed in pesticide registration ofChina. The 2^(nd)-instar larvae of Bombyx mori L. were used as testobjects and tested by using a leaf immersion feeding method.

Operation process: Samples were weighed accurately, and respectivelyadded with 200 μL of dimethyl sulfoxide to prepare 10 g/L mother liquorwhich was diluted into a concentration of 1000 ppm with an aqueoussolution containing 0.05% of Tween-80 during the test. Young cotyledonsof mulberries were collected, washed and air-dried, immersed in a liquidmedicine, taken out after 5 seconds, naturally air-dried, and thentransferred into a clean vessel. About 35 2^(nd)-instar larvae of Bombyxmori L. were put into the vessel and fed at a constant temperature of25° C. Each concentration was repeated 3 times, and an aqueous solutioncontaining 0.05% of Tween-80 was used as a control group. After beingtreated for 24 hours, a number of dead Plutella xylostella was counted,and a mortality (%) was calculated according to a formula that mortality(%)=(number of live larvae in the control group—number of treated livelarvae)/number of live larvae in the control group*100%. The resultswere shown in Table 10.

(2) Toxicity Test on Adult Worker Bees of Apis cernan.

Adult worker bees of Apis cernan having the same size were selected fortest. The worker bees were collected from beekeeping boxes in thedaystart of the test day and tested by using a small beaker method.

Operation process: A small amount of absorbent cotton was put into a 5mL small beaker, 5 mL of a test liquid medicine (a concentration of 500ppm) was dropped into the absorbent cotton, and stirred gently to makethe absorbent cotton completely wet but not leached obviously, then thesmall beaker was put into a 500 mL large beaker, then 15 worker beeswere put into the large beaker, and finally the large beaker was sealedwith gauze. After treatment, the large beaker was placed in a dark roomof an artificial climate box. After taking the medicine for 48 hours, anumber of live and dead worker bees were investigated. The results wereshown in Table 25.

TABLE 25 Toxicity of Some Compounds of Formula (I) Shown in Table 1 toTable 3 on Environmental Non-target Organisms Toxicity determinationToxicity determination Bombyx mori L. Apis cernan Bombyx mori L. Apiscernan Compound Mortality (%) Mortality (%) Mortality (%) Mortality (%)No. 1000 ppm 500 ppm Compound No. 1000 ppm 500 ppm A1 9 12 A22 0 3 A4 108 A23 0 5 A5 2 9 A26 7 10 A7 6 6 A27 10 15 A8 12 10 A30 8 8 A10 15 12A32 10 4 A12 13 12 A36 3 0 A13 17 17 A43 3 8 A15 8 5 A44 8 8 A19 7 5 A4510 11 A21 0 6 A46 7 2 B1 0 0 B7 6 6 B2 3 4 B8 5 4 B3 0 3 B9 0 5 B4 0 0B10 3 3 B5 6 4 B11 7 3 B6 4 5 B12 5 6 C1 7 7 C32 6 9 C2 5 10 C35 4 4 C312 10 C36 2 3 C4 3 0 C37 6 8 C9 8 9 C38 4 0 C10 10 9 C40 4 4 C13 12 10C43 0 4 C14 10 10 C45 6 3 C15 8 7 C46 5 3 C18 6 5 C50 5 2 C20 8 10 C51 95 C24 11 10 C52 10 7 C25 3 0 C56 6 8 C26 4 4 C58 4 4 C29 0 4 C61 9 10C30 0 0 C62 10 11 C31 3 8 C64 7 9

Embodiment 11: Preparation of Insecticide Composition Containing theCompound of the Present Invention

(1) Oily Suspension.

The following components were prepared in proportion: 25% (weightpercentage, same below) of any one of the above compounds; 5% ofpolyoxyethylene sorbitan hexaoleate; and 70% of higher aliphatichydrocarbon oil. The components were ground together in a sand milluntil sizes of solid particles were 5 μm or less. The viscous suspensionobtained could either be used directly, or used after being emulsifiedin water.

(2) Aqueous Suspension.

The following components were prepared in proportion: 25% of any one ofthe above compounds; 3% of hydrated attapulgite; 10% of calciumlignosulfonate; 0.5% of sodium dihydrogenphosphate; and 61.5% of water.The components were ground together in a ball mill until sizes of solidparticles were approximately 10 μm or less. The aqueous suspension couldbe used directly.

(3) Bait.

The following components were prepared in proportion: 0.1 o 10% of anyone of the above compounds; 80% of wheat flour; and 19.9 to 10% ofmolasses. These components were completely mixed to form a bait shape asrequired. The edible baits could be dispersed to places infested bysanitary insect pests, for example, furniture or industrial places, suchas kitchens, hospitals or shops or outdoor areas, so as to control thepests by oral ingestion.

Finally, it should be noted that the above embodiments are only used toillustrate the technical solutions of the present invention, but are notintended to limit the scope of protection of the present invention.Those of ordinary skill in the art can make other different forms oftransformations or changes based on the above description and ideas. Allthe embodiments need not and cannot be exhaustive here. Anymodifications, equivalent substitutions, and improvements made withinthe spirit and principle of the present invention shall all fall withinthe scope of protection of the claims of the present invention.

1. A fused heterocyclic compound, and an optical isomer, cis and transisomers or an agromedically acceptable salt thereof, the fusedheterocyclic compound comprises a structure shown in formula (I):

wherein R¹¹ and R¹² are each independently hydrogen, halogen, —NO₂, —CN,—COR¹⁷, —CO₂R¹⁷, —CONR¹⁷R¹⁸, —S(O) R¹⁷, —S(O)₂ R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷COR¹⁸, —N R¹⁷CON R¹⁸R¹⁹, —N R¹⁷CO₂ R¹⁸, —N R¹⁷S(O)₂ R¹⁸, alkyl,heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl orheteroaryl; wherein the alkyl, the alkenyl, the cycloalkyl, thecycloalkenyl, the aryl, the heterocyclyl or the heteroaryl isunsubstituted or substituted with one or more substituents R¹⁰; R¹³ ishydrogen, —COR⁷, —CO₂ R¹⁷, —S(O)₂ R¹⁷, —CONR¹⁷R¹⁸, alkyl, heteroalkyl,alkenyl, cycloalkyl, cycloalkenyl and aryl; wherein the alkyl, thealkenyl, the cycloalkyl, the cycloalkenyl and the aryl are unsubstitutedor substituted with one or more substituents R¹⁰; R¹⁴ and R¹⁵ are eachindependently hydrogen, halogen, —CN, —OH, —N R¹⁷ R¹³, —O R¹⁷, —CO R¹⁷,—CO₂ R¹⁷, —CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CON R¹⁸R¹⁹, —NR¹⁷CO₂R¹⁸,—NR¹⁷S(O)₂R¹⁸, —S(O)R¹⁷, —S(O)₂R¹⁷, alkyl, heteroalkyl, alkenyl,cycloalkyl, cycloalkenyl, aryl, heterocyclyl or heteroaryl; wherein thealkyl, the alkenyl, the cycloalkyl, the cycloalkenyl, the aryl, theheterocyclyl or the heteroaryl is unsubstituted or substituted with oneor more substituents R¹⁰, and R¹⁴ and R's are not hydrogen at the sametime; Y is N or CH; Z¹, Z², Z³ and Z⁴ are each independently C or N,under conditions that at most two of Z¹ to Z⁴ are N, and a ringcontaining Z¹ to Z⁴ is aromatic; R¹⁶ represents a substituent on thering containing Z¹ to Z⁴, one or more R¹⁶ are provided, and each R¹⁶ isindependently hydrogen, halogen, —CN, alkyl, heteroalkyl, —CO R¹⁷, —CO₂R¹⁷, —N R¹⁷ R¹⁸, —CONR¹⁷R, —N R¹⁷CO R¹⁸, —NR⁷CON R¹⁸R¹⁹, —NR¹⁷CO₂R¹⁸ orNR¹⁷S(O)₂R¹⁸; R¹⁷, R¹⁸ and R¹⁹ are each independently hydrogen, alkyl,heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl orheteroaryl; wherein the alkyl, the alkenyl, the cycloalkyl, thecycloalkenyl, the aryl, the heterocyclyl or the heteroaryl isunsubstituted or substituted with one or more substituents R¹⁰; and R¹⁰is halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, substituted or unsubstitutedcycloalkyl, cycloalkenyl, substituted or unsubstituted aryl, substitutedor unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl,—CN, —NH₂, —OR′″, —NR′R″″, —COR′″, —CO₂R′″, —CONR′″R″″, —NR′″COR″″,—NR′″CONR′″R″″, —NR′″CO₂R″″, —S(O)₂R′″ or —NR′″S(O)₂R″″, wherein R′″ andR″″ are each independently hydrogen, C₁-C₆ alkyl, C₂-C₆ alkenyl,cycloalkyl, cycloalkenyl, aryl, heteroaryl or heterocyclyl.
 2. Thecompound according to claim 1, or the optical isomer, the cis and transisomers or the agromedically acceptable salt of the compound, whereinwhen Y is N or CH; R¹¹ is halogen, —CN, —COR¹⁷, —CONR¹⁷R¹⁸, —S(O) R¹⁷,—N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸, aryl, heterocyclyl or heteroaryl; wherein thearyl, the heterocyclyl or the heteroaryl is unsubstituted or substitutedwith one or more substituents R¹⁰; R¹² is hydrogen, —COR¹⁷, —CONR¹⁷R¹⁸,—S(O)R¹⁷, —S(O)₂R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CONR¹⁸R¹⁹,—NR⁷CO₂R¹⁸, aryl, heterocyclyl or heteroaryl; wherein the aryl, theheterocyclyl or the heteroaryl is unsubstituted or substituted with oneor more substituents R¹⁰; R¹³ is hydrogen, —COR¹⁷, alkyl, heteroalkyl oralkenyl; R¹⁴ is halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷, —CO R¹⁷, —CO₂ R¹⁷,—CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl or alkenyl;wherein the alkyl, the heteroalkyl or the alkenyl is unsubstituted orsubstituted with one or more substituents R¹⁰; and R¹⁵ is hydrogen,halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷, —CO R¹⁷, —CO₂ R¹⁷, —CONR¹⁷R¹⁸, —NR¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl or alkenyl; wherein thealkyl, the heteroalkyl or the alkenyl is unsubstituted or substitutedwith one or more substituents R¹⁰.
 3. The compound according to claim 1,or the optical isomer, the cis and trans isomers or the agromedicallyacceptable salt of the compound, wherein when Z¹, Z², Z³ and Z⁴ are allC, one or more R¹⁶ are provided, and each R¹⁶ is independently hydrogen,halogen, alkyl, heteroalkyl, alkenyl, —S(O) R¹⁷, —S(O)₂ R¹⁷, —COR¹⁷, —NR¹⁷ R¹⁸, —CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸ or —NR¹⁷S(O)₂R¹⁸; R¹¹ is halogen, —CN,—COR¹⁷, —CONR¹⁷R¹⁸, —S(O) R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸, aryl,heterocyclyl or heteroaryl; wherein the aryl, the heterocyclyl or theheteroaryl is unsubstituted or substituted with one or more substituentsR¹⁰; R¹² is —CONR¹⁷R¹⁸, —S(O) R¹⁷, —S(O)₂ R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸,—N R¹⁷CON R¹⁸R¹⁹, aryl, heterocyclyl or heteroaryl; wherein the aryl,the heterocyclyl or the heteroaryl is unsubstituted or substituted withone or more substituents R¹⁰; R¹³ is hydrogen, —COR¹⁷, alkyl or alkenyl;and R¹⁴ and R¹⁵ are each independently halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷,—CO R¹⁷, —CO₂ R¹⁷, —CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl,heteroalkyl and alkenyl; wherein the alkyl, the heteroalkyl and thealkenyl is unsubstituted or substituted with one or more substituentsR¹⁰.
 4. The compound according to claim 1, or the optical isomer, thecis and trans isomers or the agromedically acceptable salt of thecompound, wherein, when Y is N or CH; R¹¹ is halogen, —CN, —COR¹⁷,—CONR¹⁷R¹⁸, —S(O) R¹⁷, —N R¹⁷ R¹⁸ or —N R¹⁷CO R¹⁸; R¹² is —S(O) R¹⁷,—S(O)₂ R¹⁷, —N R¹⁷ R¹⁸, —N R¹⁷CO R¹⁸, aryl or heteroaryl; wherein thearyl or the heteroaryl is unsubstituted or substituted with one or moresubstituents R¹⁰; R¹³ is hydrogen, —COR¹⁷, alkyl or alkenyl; R¹⁴ and R¹⁵are each independently halogen, —CN, —N R¹⁷ R¹⁸, —O R¹⁷, —CO R¹⁷, —CO₂R¹⁷, —CONR¹⁷R¹⁸, —N R¹⁷CO R¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl oralkenyl; wherein the alkyl or the alkenyl is unsubstituted orsubstituted with one or more substituents R¹⁰; and Z¹, Z², Z³ and Z⁴ areall C, one or more R¹⁶ are provided, and each R¹⁶ is independentlyhalogen, alkyl, heteroalkyl, —S(O) R¹⁷, —S(O)₂ R¹⁷, —COR¹⁷, —N R¹⁷R¹⁸,—N R¹⁷CO R¹⁸ or —NR¹⁷S(O)₂R¹⁸.
 5. The compound according to claim 4, orthe optical isomer, the cis and trans isomers or the agromedicallyacceptable salt of the compound, wherein, R¹¹ is halogen, —CN, —COR¹⁷ or—CONR¹⁷R¹⁸; R¹² is —S(O)R¹⁷, —S(O)₂R¹⁷, —NR¹⁷COR¹⁸, aryl or heteroaryl;wherein the aryl or the heteroaryl is unsubstituted or substituted withone or more substituents R¹⁰; R¹³ is hydrogen, —COR¹⁷ or alkyl; and Z¹,Z², Z³ and Z⁴ are all C, one or more R¹⁶ are provided, and each R¹⁶ isindependently halogen, heteroalkyl, —S(O)R¹⁷, —NR¹⁷R¹⁸ or —NR¹⁷COR¹⁸. 6.The compound according to claim 4, or the optical isomer, the cis andtrans isomers or the agromedically acceptable salt of the compound,wherein R¹¹ is —CN or —COR¹⁷; R¹² is —S(O)R¹⁷ or aryl; wherein the arylis substituted with one or more substituents R¹⁰; R¹³ is hydrogen,—COR¹⁷, methyl or ethyl; R¹⁴ and R¹⁵ are each independently halogen,—OR¹⁷, —COR¹⁷, —CO₂R¹⁷, —CONR¹⁷R¹⁸, —NR¹⁷COR¹⁸, —NR¹⁷CO₂R¹⁸, alkyl,heteroalkyl or alkenyl; wherein the alkyl or the alkenyl isunsubstituted or substituted with one or more substituents R¹⁰; and Z¹,Z², Z³ and Z⁴ are all C, one or more R¹⁶ are provided, and each R¹⁶ isindependently halogen or heteroalkyl.
 7. The compound according to claim4, or the optical isomer, the cis and trans isomers or the agromedicallyacceptable salt of the compound, wherein, R¹¹ is —CN or —COR¹⁷, and R¹⁷is alkyl or heteroalkyl; R¹² is —S(O)R¹⁷, and R¹⁷ is alkyl orheteroalkyl; R¹³ is hydrogen, —COR¹⁷, methyl or ethyl, and R¹⁷ is alkyl;R¹⁴ and R¹⁵ are each independently halogen, —OR¹⁷, —COR¹⁷, —CO₂R¹⁷,—CONR¹⁷R¹⁸, —NR¹⁷COR¹⁸, —NR¹⁷CO₂R¹⁸, alkyl, heteroalkyl or alkenyl;wherein the alkyl or the alkenyl is unsubstituted or substituted withone or more substituents R¹⁰; and Z¹, Z², Z³ and Z⁴ are all C, one ormore R¹⁶ are provided, and each R¹⁶ is independently halogen orheteroalkyl.
 8. A pyrazole-ring-containing fused heterocyclic compound,and an optical isomer, cis and trans isomers or an agromedicallyacceptable salt thereof, the pyrazole-ring-containing fused heterocycliccompound comprising a structure shown in formula (II):

wherein R¹ is hydrogen, halogen, —CN, alkyl, heteroalkyl, aryl orheteroaryl; wherein the alkyl, the aryl or the heteroaryl isunsubstituted or substituted with one or more substituents R⁹; R² ishydrogen, halogen, —CN, —S(O)R⁷, —S(O)₂R⁷, alkyl, heteroalkyl, aryl orheteroaryl; wherein the alkyl, the aryl or the heteroaryl isunsubstituted or substituted with one or more substituents R⁹; R³ ishydrogen, —COR⁷, alkyl or heteroalkyl; R⁴ and R⁵ are each independentlyhydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷, —CH₂COOR⁷, amino,alkyl, heteroalkyl, aryl or heteroaryl; wherein the amino, the alkyl,the aryl or the heteroaryl is unsubstituted or substituted by one ormore substituents R⁹, and R⁴ and R⁵ are not hydrogen at the same time;Z¹ and Z² are each independently C or N, and are not N at the same time,and a ring containing Z¹ and Z² is an aromatic ring; R⁶ represents asubstituent on the ring containing Z¹ and Z², one or more R⁶ areprovided, and each R⁶ is independently hydrogen, halogen, —NO₂, —CN,alkyl, heteroalkyl, —OR⁷, —COR⁷, —CO₂R⁷ or —NR⁷R⁸; R⁷ and R⁸ are eachindependently hydrogen, hydroxyl, amino, C₁-C₆ alkyl, heteroalkyl, arylor heteroaryl; wherein the alkyl, the aryl or the heteroaryl isunsubstituted or substituted with one or more substituents R⁹; and R⁹ ishalogen, C₁-C₆ alkyl, heteroalkyl, —CN, —NH₂, —OH, —COR′, —CO₂R′ or—CONR′R″, wherein R′ and R″ are independently hydrogen, C₁-C₆ alkyl orheteroalkyl.
 9. The compound according to claim 8, or the opticalisomer, the cis and trans isomers or the agromedically acceptable saltof the compound, wherein, when Z¹ is N and Z² is C, R⁶ is amonosubstituent —CF₃ at a 5-position of a pyridine ring, and the generalformula of the compound is shown in formula (a):

wherein R³ is hydrogen, methyl or chloromethyl; R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted by one or more substituents R⁹; or, when Z² is N and Z¹ isC, R⁶ is a monosubstituent chlorine at a 5-position of the pyridinering, and the general formula of the compound is shown in formula (b):

wherein R³ is hydrogen, methyl or chloromethyl; R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹; or, when Z¹ and Z² areboth C, and R⁶ is disubstituents at a 3-position and a 5-position of abenzene ring, the general formula of the compound is shown in formula(c):

wherein R¹ is —CN or —CF₃, and R² is —CN, —CF₃, —OCF₃, —SOCF₃ or—SOCH₂CH₃; R³ is hydrogen, —CH₃, —Ac or —CH₂CH₂Cl; a substituent of R⁶at the 3-position of the benzene ring is —Cl, —Br, —CF₃, —CH₃, —CN,—CO₂CH₃ or —NO₂, and a substituent of R⁶ at the 5-position of thebenzene ring is —Cl, —CF₃, —OCF₃ or —NO₂; R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹; or, when Z¹ and Z² areboth C, R⁶ is disubstituents at a 4-position and a 6-position of thebenzene ring, and R³ is hydrogen, the general formula of the compound isshown in formula (d):

wherein R¹ is —CN, —CF₃, —COCH₃ or —CH₂NH₂, and R² is —OCF₃, —CF₃, —CN,—SOCF₃, —SOCH₃, —SOCH₂CH₃, —SOPh, —SOCH₂Ph, —SOC₆H₁₃,

R⁶ is —Cl or —CF₃; R⁴ and R⁵ are each independently hydrogen, halogen,—CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷, —CH₂COOR⁷, amino, alkyl, heteroalkyl, arylor heteroaryl; wherein the amino, the alkyl, the aryl or the heteroarylis unsubstituted or substituted with one or more substituents R⁹; or,when Z¹ and Z² are both C, R⁶ is disubstituents at the 3-position andthe 6-position, or at the 3-position and the 4-position, or at the4-position and the 5-position, or at the 5-position and the 6-positionof the benzene ring, and R³ is hydrogen, the general formula of thecompound is shown in formula (e):

wherein R¹ is —CN, and R² is —SOCF₃; R⁶ is —Cl or —CF₃; R⁴ and R⁵ areeach independently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹; and R⁴ and R⁵ are nothydrogen at the same time.
 10. The compound according to claim 9, or theoptical isomer, the cis and trans isomers or the agromedicallyacceptable salt of the compound, wherein R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl or heteroalkyl; wherein R⁷ is hydrogen, halogen,hydroxyl, C₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkenyl, C₁₋₄ haloalkenyl,amino or substituted amino.
 11. The compound according to claim 9, orthe optical isomer, the cis and trans isomers or the agromedicallyacceptable salt of the compound, wherein when the compound is shown inthe formula (a) or the formula (b), and any one of R⁴ and R⁵ ishydrogen, R¹ is —CN, and R² is —SOCF₃ or —OCF₃; or R′ is —CF₃, and R² is—SOCF₃; or, when neither R⁴ nor R⁵ is hydrogen, R¹ is —CN or —CF₃; andR² is —SOCF₃, —SOCH₂CH₃, —OCF₃, —CF₃, —CN or halogen.
 12. The compoundaccording to claim 9, or the optical isomer, the cis and trans isomersor the agromedically acceptable salt of the compound, wherein when thecompound is shown in the formula (c), R³ is —CH₃, —Ac or —CH₂CH₂Cl, R is—SOCF₃, R¹ is —CN, and both R⁴ and R⁵ are —CO₂Me; or, when R³ ishydrogen, and R² is —CN, —CF₃ or —SOCH₂CH₃, R¹ is —CN or —CF₃, and R⁴and R⁵ are each independently —CO₂Me or —CH₂CO₂Me; or, when R³ ishydrogen, and R² is —OCF₃ or —SOCF₃, R¹ is —CN or —CF₃, R⁴ and R⁵ areeach independently hydrogen, halogen, —CN, —COR⁷, —C₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹.
 13. The compound accordingto claim 9, or the optical isomer, the cis and trans isomers or theagromedically acceptable salt of the compound, wherein when the compoundis shown in the formula (d), R³ is hydrogen, and R² is —CN, —CF₃, —SOPh,—SOCH₂Ph, —SOC₆H₁₃, or

R¹ is —CN, and R⁴ and R⁵ are each independently —CO₂Me or —CO₂CH₂Me; or,when R³ is hydrogen, R² is —SOCF₃, and R is —COCH₃ or —CH₂NH₂, R⁴ and R⁵are each independently —CO₂Me or —CO₂CH₂Me; or, when R³ is hydrogen, andR² is —OCF₃ or —SOCF₃, R¹ is —CN or —CF₃, R⁴ and R⁵ are eachindependently hydrogen, halogen, —CN, —COR⁷, —CO₂R⁷, —CH₂COR⁷,—CH₂COOR⁷, amino, alkyl, heteroalkyl, aryl or heteroaryl; wherein theamino, the alkyl, the aryl or the heteroaryl is unsubstituted orsubstituted with one or more substituents R⁹.
 14. The compound accordingto claim 9, or the optical isomer, the cis and trans isomers or theagromedically acceptable salt of the compound, wherein when the compoundis shown in the formula (e), R⁶ is 3-Cl and 6-CF₃, 3-Cl and 4-CF₃, 4-Cland 5-CF₃, or 5-Cl and 6-CF₃ on the benzene ring; and R⁴ and R⁵ are eachindependently —CO₂Me, —CH₂CO₂Me, —CO₂Et, —CH₂CO₂Et, —CH₂CO₂CH₂CF₃ or—CH₂CO₂CH₂CHF₂.
 15. An agricultural composition, comprising: (a) 0.001to 99.99% by weight of the compound according to claim 1, or the opticalisomer, the cis and trans isomers or the agromedically acceptable saltthereof, or a combination thereof, and (b) an agromedically acceptablecarrier and/or excipient.
 16. A method of using the agriculturalcomposition according to claim 15 in preparing an insecticide forkilling or preventing agroforestry pests, sanitary insect pests andpests harmful to animal health.
 17. The method of using according toclaim 16, wherein the insecticide is directly applied to the pests orplaces contacted by the pests.
 18. An agricultural composition,comprising: (a) 0.001 to 99.99% by weight of the compound according toclaim 8, or the optical isomer, the cis and trans isomers or theagromedically acceptable salt thereof, or a combination thereof; and (b)an agromedically acceptable carrier and/or excipient.
 19. A method ofusing the agricultural composition according to claim 18 in preparing aninsecticide for killing or preventing agroforestry pests, sanitaryinsect pests and pests harmful to animal health.
 20. The method of usingaccording to claim 19, wherein the insecticide is directly applied tothe pests or places contacted by the pests.